Trifluromethoxyphenyl-substituted tetramic acid derivatives pesticides and/or herbicides

ABSTRACT

The present invention relates to novel trifluoromethoxyphenyl-substituted tetramic acid derivatives of the formula (I), 
                         
in which
 
J, X, Y, A, B, D and G have the meanings given above,
 
to a number of processes for their preparation, and to their use as pesticides and/or herbicides. The invention further provides selective herbicidal compositions which comprise, firstly, trifluoromethoxyphenyl-substituted tetramic acid derivatives and, secondly, a crop plant compatibility-improving compound.
 
     The invention further relates to the boosting of the action of crop protection compositions comprising compounds of the formula (I) through the additions of ammonium salts or phosphonium salts and optionally penetrants.

The present invention relates to noveltrifluoromethoxyphenyl-substituted tetramic acid derivatives, to aplurality of processes for their preparation and to their use aspesticides and/or herbicides. The invention also provides selectiveherbicidal compositions comprising, firstly, thetrifluoromethoxyphenyl-substituted tetramic acid derivatives and,secondly, a crop plant compatibility-improving compound.

The present invention further relates to the boosting of the action ofcrop protection compositions comprising, in particular,trifluoromethoxyphenyl-substituted tetramic acid derivatives, throughthe addition of ammonium salts or phosphonium salts and optionallypenetrants, to the corresponding compositions, to processes forproducing them and to their application in crop protection asinsecticides and/or acaricides and/or for preventing unwanted plantgrowth.

For 3-acylpyrrolidine-2,4-diones pharmaceutical properties have beenpreviously described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have beensynthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem.1985, 1095). Biological activity of these compounds has not beendescribed.

EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structuredcompounds (3-arylpyrrolidine-2,4-diones) for which, however, noherbicidal, insecticidal or acaricidal action has been disclosed. Knowncompounds with herbicidal, insecticidal or acaricidal action areunsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives(EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) and also substitutedmonocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 andEP-A-442 077).

Additionally known are polycyclic 3-arylpyrrolidine-2,4-dionederivatives (EP-A-442 073) and also 1H-arylpyrrolidinedione derivatives(EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885,WO 94/01997, WO 95/26954, WO 95/20572, EP-A-0 668 267, WO 96/25395, WO96/35664, WO 97/01535, WO 97/02243, WO 97/36868, WO 97/43275, WO98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO99/43649, WO 99/48869, WO 99/55673, WO 01/17972, WO 01/23354, WO01/74770, WO 03/013249, WO 04/007448, WO 04/024688, WO 04/065366, WO04/080962, WO 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO05/049596, WO 05/066125, WO 05/092897, WO 06/000355, WO 06/029799, WO06/056281, WO 06/056282, WO 06/089633, WO 07/048,545, WO 07/073,856,DE-A-05/059892, DE-A-06/007882, DE-A-06/018828, DE-A-06/025874).

However, in particular at low application rates and concentrations, theactivity and activity spectrum of these compounds is not always fullysatisfactory. Furthermore, the compatibility of these compounds withsome crop plants is not always sufficient.

This invention now provides novel compounds of the formula (I)

in whichJ represents trifluoromethoxy,X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,Y represents hydrogen, alkyl, alkoxy or halogen,with the proviso, that at least one of the radicals J, X and Y islocated in the 2-position of the phenyl radical and is not hydrogen,

-   -   A represents hydrogen, in each case optionally        halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl,        saturated or unsaturated, optionally substituted cycloalkyl in        which optionally at least one ring atom is replaced by a        heteroatom, or in each case optionally halogen-, alkyl-,        haloalkyl-, alkoxy-, haloalkoxy-, cyano- or nitro-substituted        aryl, arylalkyl or hetaryl,    -   B represents hydrogen, alkyl or alkoxyalkyl, or    -   A and B together with the carbon atom to which they are attached        represent a saturated or unsaturated, unsubstituted or        substituted cycle which optionally contains at least one        heteroatom,    -   D represents hydrogen or an optionally substituted radical from        the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl,        saturated or unsaturated cycloalkyl in which optionally one or        more ring members are replaced by heteroatoms, arylalkyl, aryl,        hetarylalkyl or hetaryl or    -   A and D together with the atoms to which they are attached        represent a saturated or unsaturated cycle which optionally        contains at least one heteroatom and which is unsubstituted or        substituted in the A, D moiety,    -   G represents hydrogen (a) or represents one of the groups

-   -   -   in which        -   E represents a metal ion equivalent or an ammonium ion,        -   L represents oxygen or sulphur,        -   M represents oxygen or sulphur,        -   R¹ represents in each case optionally halogen-substituted            alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl            or optionally halogen-, alkyl- or alkoxy-substituted            cycloalkyl which may be interrupted by at least one            heteroatom, in each case optionally substituted phenyl,            phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,        -   R² represents in each case optionally halogen-substituted            alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents            in each case optionally substituted cycloalkyl, phenyl or            benzyl,        -   R³, R⁴ and R⁵ independently of one another represent in each            case optionally halogen-substituted alkyl, alkoxy,            alkylamino, dialkylamino, alkylthio, alkenylthio,            cycloalkylthio or represent in each case optionally            substituted phenyl, benzyl, phenoxy or phenylthio,        -   R⁶ and R⁷ independently of one another represent hydrogen,            in each case optionally halogen-substituted alkyl,            cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent            optionally substituted phenyl, represent optionally            substituted benzyl, or together with the nitrogen atom to            which they are attached represent a cycle which is            optionally interrupted by oxygen or sulphur.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) may be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if appropriate, may beseparated in a customary manner. The present invention provides for thepure isomers and the isomer mixtures, their preparation and use andcompositions comprising them. However, for the sake of simplicity,hereinbelow only compounds of the formula (I) are referred to, althoughwhat is meant are both the pure compounds and, if appropriate, mixtureshaving various proportions of isomeric compounds.

Including the different meanings (a), (b), (c), (d), (e), (f) and (g) ofgroup G, the following principal structures (I-a) to (I-g) result

in whichA, B, D, E, J, L, M, X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have themeanings given above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by one of the processes described below:

-   (A) Compounds of the formula (I-a)

-   -   in which    -   A, B, D, J, X and Y have the meanings given above,    -   are obtained when    -   N-acylamino acid esters of the formula (II)

-   -   in which    -   A, B, D, J, X and Y have the meanings given above,    -   and    -   R⁸ represents alkyl (preferably C₁-C₆-alkyl),    -   are condensed intramolecularly in the presence of a diluent and        in the presence of a base.

Furthermore, it has been found

-   (B) that the compounds of the formula (I-b) shown above in which A,    B, D, J, R¹, X, and Y have the meanings given above are obtained    when compounds of the formula (I-a) shown above in which A, B, D, J,    X and Y have the meanings given above are in each case reacted-   (α) with acid halides of the formula (III)

-   -   in which    -   R¹ has the meaning given above and    -   Hal represents halogen (in particular chlorine or bromine)    -   or

-   (β) with carboxylic anhydrides of the formula (IV)    R¹—CO—C—CO—R¹  (IV)    -   in which    -   R¹ has the meaning given above,    -   optionally in the presence of a diluent and if appropriate in        the presence of an acid binder;

-   (C) that the compounds of the formula (I-c) shown above in which A,    B, D, J, R², M, X and Y have the meanings given above and L    represents oxygen are obtained when compounds of the formula (I-a)    shown above in which A, B, D, J, X and Y have the meanings given    above are in each case reacted    -   with chloroformic esters or chloroformic thioesters of the        formula (V)        R²-M-CO—Cl  (V)    -   in which    -   R² and M have the meanings given above,    -   optionally in the presence of a diluent and optionally in the        presence of an acid binder;

-   (D) that compounds of the formula (I-c) shown above in which A, B,    D, J, R², M, X and Y have the meanings given above and L represents    sulphur are obtained when compounds of the formula (I-a) shown above    in which A, B, D, J, X and Y have the meanings given above are in    each case reacted    -   with chlormonothioformic esters or chlordithioformic esters of        the formula (VI)

-   -   in which    -   M and R² have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder    -   and

-   (E) that compounds of the formula (I-d) shown above in which A, B,    D, J, R³, X and Y have the meanings given above are obtained when    compounds of the formula (I-a) shown above in which A, B, D, J, X    and Y have the meanings given above are in each case reacted    -   with sulphonyl chlorides of the formula (VII)        R³—SO₂—Cl  (VII)    -   in which    -   R³ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (F) that compounds of the formula (I-e) shown above in which A, B,    D, J, L, R⁴, R⁵, X and Y have the meanings given above are obtained    when compounds of the formula (I-a) shown above in which A, B, D, J,    X and Y have the meanings given above are in each case reacted    -   with phosphorus compounds of the formula (VIII)

-   -   in which    -   L, R⁴ and R⁵ have the meanings given above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (G) that compounds of the formula (I-f) shown above in which A, B,    D, E, J, X and Y have the meanings given above are obtained when    compounds of the formula (I-a) in which A, B, D, J, X and Y have the    meanings given above are in each case reacted    -   with metal compounds or amines of the formulae (IX) and (X),        respectively,

-   -   in which    -   Me represents a mono- or divalent metal (preferably an alkali        metal or alkaline earth metal, such as lithium, sodium,        potassium, magnesium or calcium), or represents an ammonium ion

-   -   t represents the number 1 or 2 and    -   R¹⁰, R¹¹, R¹² independently of one another represent hydrogen or        alkyl (preferably C₁-C₈-alkyl),    -   if appropriate in the presence of a diluent,

-   (H) that compounds of the formula (I-g) shown above in which A, B,    D, J, L, R⁶, R⁷, X and Y have the meanings given above are obtained    when compounds of the formula (I-a) shown above in which A, B, D, J,    X and Y have the meanings given above are in each case reacted

-   (α) with isocyanates or isothiocyanates of the formula (XI)    R⁶—N═C=L  (XI)    -   in which    -   R⁶ and L have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or

-   (β) with carbamoyl chlorides or thiocarbamoyl chlorides of the    formula (XII)

-   -   in which    -   L, R⁶ and R⁷ have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder.

The following compounds of the formula (I) have been disclosed in thecontext of the European patent examination proceedings relating toEP-A-809629 and EP-A-915846:

From EP-A-809629

Ex. No. A B G Isomer I-1-a-13 —(CH₂)₂—CHCH₃—(CH₂)₂— H β I-1-a-14—(CH₂)₂—CHOCH₃—(CH₂)₂ H β I-1-b-14 —(CH₂)₂—CHCH₃—(CH₂)₂ CO-i-C₃H₇ βI-1-b-15 —(CH₂)₂—CHCH₃—(CH₂)₂— CO-CH₂-t-C₄H₉ β I-1-b-16—(CH₂)₂—CHOCH₃—(CH₂)₂— CO-i-C₃H₇ β I-1-b-17 —(CH₂)₂—CHOCH₃—(CH₂)₂CO-CH₂-t-C₄H₉ β I-1-c-9 —(CH₂)₂—CHCH₃—(CH₂)₂— CO₂C₂H₅ β I-1-c-10—(CH₂)₂—CHOCH₃—(CH₂)₂ CO₂C₂H₅ βFrom EP-A-915846

Furthermore, it has been found that the novel compounds of the formula(I) are very effective as pesticides, preferably as insecticides,acaricides and/or herbicides.

Surprisingly, it has now also been found that certain substituted cyclicketoenols, when used together with the crop plantcompatibility-improving compounds (safeners/antidotes) described below,efficiently prevent damage to the crop plants and can be used in aparticularly advantageous manner as broad-spectrum combinationpreparations for the selective control of unwanted plants in crops ofuseful plants, such as, for example, in cereals, but also in maize, soyabeans and rice.

The invention also provides selective herbicidal compositions comprisingan effective amount of an active compound combination comprising, ascomponents,

-   (a′) at least one trifluoromethoxyphenyl-substituted tetramic acid    derivative of the formula (I) in which A, B, D, G, J, X and Y have    the meaning given above    and-   (b′) at least one crop plant compatibility-improving compound from    the following group of compounds:

4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one(dicyclonon, BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl—cf.also related compounds in EP-A-86750, EP-A-94349, EP-A-191736,EP-A-492366), 3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea(cumyluron), α-(cyanomethoximino)phenylacetonitrile (cyometrinil),2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyricacid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)-urea(daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenyl-amino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 andEP-A-346620), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine(furilazole, MON-13900), ethyl4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl—cf.also related compounds in WO-A-95/07897), 1-(ethoxycarbonyl)ethyl3,6-dichloro-2-methoxybenzoate (lactidichlor),(4-chloro-o-tolyloxy)acetic acid (MCPA),2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874)2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),1,8-naphthalic anhydride,α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid,diphenylmethoxy-acetic acid, methyl diphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf.also related compounds in EP-A-269806 and EP-A-333131), ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. alsorelated compounds in WO-A-91/08202), 1,3-dimethylbut-1-yl5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate,ethyl 5-chloroquinoline-8-oxyacetate, allyl5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate,diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl5-chloroquinoline-8-oxymalonate (cf. also related compounds inEP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415, cf.EP-A-613618), 4-chlorophenoxy-acetic acid,3,3′-dimethyl-4-methoxybenzophenone,1-bromo-4-chloromethylsulphonylbenzene,1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (also known asN-(2-methoxy-benzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide),1-[4-(N-2-methoxybenzoyl-sulphamoyl)phenyl]-3,3-dimethylurea,1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide,

and/or one of the following compounds, defined by general formulae

of the general formula (IIa)

or of the general formula (IIb)

or of the formula (IIc)

where

-   m represents a number 0, 1, 2, 3, 4 or 5,-   A¹ represents one of the divalent heterocyclic groupings shown    below,

-   n represents a number 0, 1, 2, 3, 4 or 5,-   A² represents optionally C₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl-    and/or C₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2    carbon atoms,-   R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)-amino,-   R¹⁵ represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy,    C₁-C₆-alkenyloxy, C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylamino or di(C₁-C₄-alkyl)-amino,-   R¹⁶ represents optionally fluorine-, chlorine- and/or    bromine-substituted C₁-C₄-alkyl,-   R¹⁷ represents hydrogen, in each case optionally fluorine-,    chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl,-   R¹⁸ represents hydrogen, in each case optionally fluorine-,    chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl,-   R¹⁷ and R¹⁸ also together represent C₃-C₆-alkanediyl or    C₂-C₅-oxaalkanediyl, each of which is optionally substituted by    C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or by two    substituents which, together with the C atom to which they are    attached, form a 5- or 6-membered carbocycle,-   R¹⁹ represents hydrogen, cyano, halogen, or represents in each case    optionally fluorine-, chlorine- and/or bromine-substituted    C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,-   R²⁰ represents hydrogen, optionally hydroxyl-, cyano-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl or    tri-(C₁-C₄-alkyl)-silyl,-   R²¹ represents hydrogen, cyano, halogen, or represents in each case    optionally fluorine-, chlorine- and/or bromine-substituted    C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,-   X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    and/or the following compounds, defined by general formulae    of the general formula (IId)

or of the general formula (IIe)

where

-   t represents a number 0, 1, 2, 3, 4 or 5,-   v represents a number 0, 1, 2, 3, 4 or 5,-   R²² represents hydrogen or C₁-C₄-alkyl,-   R²³ represents hydrogen or C₁-C₄-alkyl,-   R²⁴ represents hydrogen, in each case optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylamino or di(C₁-C₄-alkyl)-amino, or in each case    optionally cyano-, halogen- or C₁-C₄-alkyl-substituted    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or    C₃-C₆-cycloalkylamino,-   R²⁵ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,-   R²⁶ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or    optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,    C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally C₁-C₄-alkyl-substituted    C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl,-   X⁴ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy, and-   X⁵ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

-   J preferably represents trifluoromethoxy,-   X preferably represents hydrogen, halogen, C₁-C₆-alkyl,    C₁-C₄-haloalkyl, C₁-C₆-alkoxy or C₁-C₄-haloalkoxy,-   Y preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy or    halogen,    with the proviso, that at least one of the radicals J, X and Y is    located in the 2-position of the phenyl radical and is not hydrogen.

Here, the radicals J, X and Y, having their preferred meanings, arepreferably arranged in the phenyl substitution patterns below

where in the phenyl substitution patterns (C), (D) and (E) X and Y aresimultaneously not hydrogen,

-   A preferably represents hydrogen or in each case optionally    halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,    C₁-C₁₀-alkoxy-C₁-C₈-alkyl, C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally    halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl    in which optionally one or two not directly adjacent ring members    are replaced by oxygen and/or sulphur or represents in each case    optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,    C₁-C₆-haloalkoxy-, cyano- or nitro-substituted phenyl, naphthyl,    hetaryl having 5 to 6 ring atoms (for example furanyl, pyridyl,    imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl or thienyl),    phenyl-C₁-C₆-alkyl or naphthyl-C₁-C₆-alkyl,-   B preferably represents hydrogen, C₁-C₁₂-alkyl or    C₁-C₈-alkoxy-C₁-C₆-alkyl or-   A, B and the carbon atom to which they are attached preferably    represent saturated C₃-C₁₀-cycloalkyl or unsaturated    C₅-C₁₀-cycloalkyl in which optionally one ring member is replaced by    oxygen or sulphur and which are optionally mono- or disubstituted by    C₁-C₈-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl-C₁-C₂-alkoxy, C₃-C₁₀-cycloalkyl, C₁-C₈-haloalkyl,    C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or phenyl or-   A, B and the carbon atom to which they are attached preferably    represent C₃-C₆-cycloalkyl which is substituted by an alkylenediyl    group which is optionally substituted by C₁-C₄-alkyl and optionally    contains one or two not directly adjacent oxygen and/or sulphur    atoms, or by an alkylenedioxyl or by an alkylenedithioyl group    which, together with the carbon atom to which it is attached, forms    a further five- to eight-membered ring or-   A, B and the carbon atom to which they are attached preferably    represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which two    substituents together with the carbon atoms to which they are    attached represent in each case optionally C₁-C₆-alkyl-,    C₁-C₆-alkoxy- or halogen-substituted C₂-C₆-alkanediyl,    C₂-C₆-alkenediyl or C₄-C₆-alkanedienediyl in which optionally one    methylene group is replaced by oxygen or sulphur,-   D preferably represents hydrogen, in each case optionally    halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,    C₁-C₁₀-alkoxy-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,    C₁-C₄-alkoxy- or C₁-C₄-haloalkyl-substituted C₃-C₈-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur or    in each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,    C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, cyano- or nitro-substituted    phenyl, hetaryl having 5 or 6 ring atoms (for example furanyl,    imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl,    thienyl or triazolyl), phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl    having 5 or 6 ring atoms (for example furanyl, imidazolyl, pyridyl,    thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl or triazolyl) or-   A and D together preferably represent in each case optionally    substituted C₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which optionally    one methylene group is replaced by a carbonyl group, oxygen or    sulphur,    -   possible substituents being in each case:    -   halogen, hydroxyl, mercapto or in each case optionally        halogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,        C₃-C₇-cycloalkyl, phenyl or benzyloxy, or a further        C₃-C₆-alkanediyl grouping, C₃-C₆-alkenediyl grouping or a        butadienyl grouping which is optionally substituted by        C₁-C₆-alkyl or in which optionally two adjacent substituents        together with the carbon atoms to which they are attached form a        further saturated or unsaturated cycle having 5 or 6 ring atoms        (in which case they represent, for example, groups AD-1 to AD-10        mentioned below) which may contain oxygen or sulphur or which        optionally contains one of the following groups

-   G preferably represents hydrogen (a) or represents one of the groups

in particular (a), (b), (c) or (g)

-   -   in which    -   E represents a metal ion equivalent or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ preferably represents in each case optionally halogen-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,    C₁-C₈-alkylthio-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or    optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted    C₃-C₈-cycloalkyl in which optionally one or more (preferably not    more than two) not directly adjacent ring members are replaced by    oxygen and/or sulphur,    -   represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,    -   represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or C₁-C₆-haloalkoxy-substituted        phenyl-C₁-C₆-alkyl,    -   represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or        6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl,        pyrimidyl, furanyl or thienyl),    -   represents optionally halogen- or C₁-C₆-alkyl-substituted        phenoxy-C₁-C₆-alkyl or    -   represents optionally halogen-, amino- or        C₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl        (for example pyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyl or        thiazolyloxy-C₁-C₆-alkyl),

-   R² preferably represents in each case optionally halogen-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl,    poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,    -   represents optionally halogen-, C₁-C₆-alkyl- or        C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or    -   represents in each case optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or        C₁-C₆-haloalkoxy-substituted phenyl or benzyl,

-   R³ preferably represents optionally halogen-substituted C₁-C₈-alkyl    or represents in each case optionally halogen-, C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, cyano- or    nitro-substituted phenyl or benzyl,

-   R⁴ and R⁵ preferably independently of one another represent in each    case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,    C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each case    optionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,    C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,    C₁-C₄-alkyl- or C₁-C₄-haloalkyl-substituted phenyl, phenoxy or    phenylthio,

-   R⁶ and R⁷ independently of one another preferably represent    hydrogen, represent in each case optionally halogen-substituted    C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,    C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,    C₁-C₈-haloalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,    optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- or    C₁-C₈-alkoxy-substituted benzyl or together represent an optionally    C₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally    one carbon atom is replaced by oxygen or sulphur,

-   R¹³ preferably represents hydrogen, represents in each case    optionally halogen-substituted C₁-C₈-alkyl or C₁-C₈-alkoxy,    represents optionally halogen-, C₁-C₄-alkyl- or    C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one    methylene group is replaced by oxygen or sulphur, or represents in    each case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,    C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, nitro- or cyano-substituted    phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy,

-   R^(14a) preferably represents hydrogen or C₁-C₈-alkyl or

-   R¹³ and R^(14a) together preferably represent C₄-C₆-alkanediyl,

-   R^(15a) and R^(16a) are identical or different and preferably    represent C₁-C₆-alkyl or

-   R^(15a) and R^(16a) together preferably represent a C₂-C₄-alkanediyl    radical which is optionally substituted by C₁-C₆-alkyl,    C₁-C₆-haloalkyl or by optionally halogen-, C₁-C₆-alkyl-,    C₁-C₄-haloalkyl-, C₁-C₆-alkoxy-, C₁-C₄-haloalkoxy-, nitro- or    cyano-substituted phenyl,

-   R^(17a) and R^(18a) independently of one another preferably    represent hydrogen, represent optionally halogen-substituted    C₁-C₈-alkyl or represent optionally halogen-, C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, nitro- or    cyano-substituted phenyl or

-   R^(17a) and R^(18a) together with the carbon atom to which they are    attached preferably represent a carbonyl group or represent    optionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted    C₅-C₇-cycloalkyl in which optionally one methylene group is replaced    by oxygen or sulphur,

-   R^(19a) and R^(20a) independently of one another preferably    represent C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy,    C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino, di-(C₁-C₁₀-alkyl)amino or    di-(C₃-C₁₀-alkenyl)amino.

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   J particularly preferably represents trifluoromethoxy,-   X particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁-C₄-alkyl, trifluoromethyl or C₁-C₄-alkoxy,-   Y particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁-C₄-alkoxy or C₁-C₄-alkyl    with the proviso, that at least one of the radicals J, X and Y is    located in the 2-position of the phenyl radical and is not hydrogen.

Here, the radicals J, X and Y, having their particularly preferredmeanings, are particularly preferably arranged in the phenylsubstitution patterns below

where in the phenyl substitution patterns (C), (D) and (E) X and Y aresimultaneously not hydrogen,

-   A particularly preferably represents hydrogen, represents    C₁-C₆-alkyl or C₁-C₄-alkoxy-C₁-C₂-alkyl, each of which is optionally    mono- to trisubstituted by fluorine or chlorine, represents    C₃-C₆-cycloalkyl which is optionally mono- or disubstituted by    C₁-C₂-alkyl or C₁-C₂-alkoxy and which may optionally be interrupted    by an oxygen atom, represents phenyl or benzyl, each of which is    optionally mono- or disubstituted by fluorine, chlorine, bromine,    C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, cyano    or nitro,-   B particularly preferably represents hydrogen, C₁-C₄-alkyl or    C₁-C₂-alkoxyl-C₁-C₂-alkyl or-   A, B and the carbon atom to which they are attached particularly    preferably represent saturated or unsaturated C₅-C₇-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur    and which is optionally mono- or disubstituted by C₁-C₆-alkyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkoxy,    C₃-C₆-cycloalkyl-methoxy, trifluoromethyl or C₁-C₆-alkoxy, or-   A, B and the carbon atom to which they are attached particularly    preferably represent C₅-C₆-cycloalkyl which is substituted by an    alkylenediyl group which is optionally substituted by methyl or    ethyl and optionally contains one or two not directly adjacent    oxygen or sulphur atoms, or by an alkylenedioxyl or by an    alkylenedithiol group which, together with the carbon atom to which    it is attached, forms a further five- or six-membered ring, or-   A, B and the carbon atom to which they are attached particularly    preferably represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which    two substituents together with the carbon atoms to which they are    attached represent in each case optionally C₁-C₂-alkyl- or    C₁-C₂-alkoxy-substituted C₂-C₄-alkanediyl, C₂-C₄-alkenediyl or    butadienediyl,-   D particularly preferably represents hydrogen, represents    C₁-C₆-alkyl, C₃-C₆-alkenyl or C₁-C₄-alkoxy-C₂-C₃-alkyl, each of    which is optionally mono- to trisubstituted by fluorine, represents    C₃-C₆-cycloalkyl which is optionally mono- or disubstituted by    C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₂-haloalkyl and in which optionally    one methylene group is replaced by oxygen, or-   A and D together particularly preferably represent C₃-C₅-alkanediyl    in which one methylene group may be replaced by a carbonyl group,    oxygen or sulphur and which is optionally mono- or disubstituted,    possible substituents being C₁-C₂-alkyl or C₁-C₂-alkoxy or-   A and D together with the atoms to which they are attached represent    one of the groups AD-1 to AD-10:

-   G particularly preferably represents hydrogen (a) or represents one    of the groups

-   -   in which    -   E represents a metal ion equivalent or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ particularly preferably represents C₁-C₈-alkyl, C₂-C₁₈-alkenyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl or C₁-C₄-alkylthio-C₁-C₂-alkyl, each of    which is optionally mono- to trisubstituted by fluorine or chlorine,    or C₃-C₆-cycloalkyl which is optionally mono- or disubstituted by    fluorine, chlorine, C₁-C₂-alkyl or C₁-C₂-alkoxy and in which    optionally one or two not directly adjacent ring members are    replaced by oxygen,    -   represents phenyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,

-   R² particularly preferably represents C₁-C₈-alkyl, C₂-C₈-alkenyl or    C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally mono- to    trisubstituted by fluorine,    -   represents C₃-C₆-cycloalkyl which is optionally monosubstituted        by C₁-C₂-allyl or C₁-C₂-alkoxy or    -   represents phenyl or benzyl, each of which is optionally mono-        or disubstituted by fluorine, chlorine, bromine, cyano, nitro,        C₁-C₄-alkyl, C₁-C₃-alkoxy, trifluoromethyl or trifluoromethoxy,

-   R³ particularly preferably represents C₁-C₆-alkyl which is    optionally mono- to trisubstituted by fluorine or represents phenyl    which is optionally monosubstituted by fluorine, chlorine, bromine,    C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl, trifluoromethoxy, cyano    or nitro,

-   R⁴ particularly preferably represents C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,    C₃-C₄-alkenylthio, C₃-C₆-cycloalkylthio or represents phenyl,    phenoxy or phenylthio, each of which is optionally monosubstituted    by fluorine, chlorine, bromine, nitro, cyano, C₁-C₃-alkoxy,    C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio, C₁-C₃-alkyl    or trifluoromethyl,

-   R⁵ particularly preferably represents C₁-C₆-alkoxy or    C₁-C₆-alkylthio,

-   R⁶ particularly preferably represents hydrogen, C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, represents phenyl which is optionally    monosubstituted by fluorine, chlorine, bromine, trifluoromethyl,    C₁-C₄-alkyl or C₁-C₄-alkoxy, represents benzyl which is optionally    monosubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,    trifluoromethyl or C₁-C₄-alkoxy,

-   R⁷ particularly preferably represents C₁-C₆-alkyl, C₃-C₆-alkenyl or    C₁-C₆-alkoxy-C₁-C₄-alkyl,

-   R⁶ and R⁷ particularly preferably together represent an optionally    methyl- or ethyl-substituted C₄-C₅-alkylene radical in which    optionally one methylene group is replaced by oxygen or sulphur.

In the radical definitions mentioned as being particularly preferred,halogen represents fluorine, chlorine and bromine, in particularfluorine and chlorine.

-   J very particularly preferably represents trifluoromethoxy,-   X very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,-   Y very particularly preferably represents hydrogen, chlorine,    bromine, methyl, ethyl or methoxy,    with the proviso, that at least one of the radicals J, X and Y is    located in the 2-position of the phenyl radical and is not hydrogen.

Here, the radicals J, X and Y, having their very particularly preferredmeanings, are very particularly preferably arranged in the phenylsubstitution patterns below

-   A very particularly preferably represents hydrogen, represents    C₁-C₄-alkyl or C₁-C₂-alkoxy-C₁-C₂-alkyl, each of which is optionally    mono- to trisubstituted by fluorine, represents cyclopropyl,    cyclopentyl or cyclohexyl, represents in each case optionally    fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-,    isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-,    cyano- or nitro-substituted phenyl or benzyl,-   B very particularly preferably represents hydrogen, methyl or ethyl    or-   A, B and the carbon atom to which they are attached very    particularly preferably represent saturated C₅-C₆-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur    and which is optionally monosubstituted by methyl, ethyl, propyl,    isopropyl, methoxymethyl, ethoxymethyl, propoxymethyl,    trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, methoxyethyl,    ethoxyethyl, methoxyethoxy, ethoxyethoxy, cyclopropylmethoxy,    cyclopentylmethoxy or cyclohexylmethoxy, or-   A, B and the carbon atom to which they are attached very    particularly preferably represent C₆-cycloalkyl which is optionally    substituted by an alkylenedioxyl group which contains two not    directly adjacent oxygen atoms, or-   A, B and the carbon atom to which they are attached very    particularly preferably represent C₅-C₆-cycloalkyl or    C₅-C₆-cycloalkenyl in which two substituents together with the    carbon atoms to which they are attached represent C₂-C₄-alkanediyl    or C₂-C₄-alkenediyl or butadienediyl,-   D very particularly preferably represents hydrogen, represents    C₁-C₄-alkyl, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₂-C₃-alkyl, represents    cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally    mono- to trisubstituted by fluorine,    or-   A and D together very particularly preferably represent    C₃-C₅-alkanediyl which is optionally monosubstituted by methyl or    methoxy and in which optionally one carbon atom is replaced by    oxygen or sulphur, or represent the group AD-1,-   G very particularly preferably represents hydrogen (a) or represents    one of the groups

-   -   —SO₂—R³ (d) or E (f), in particular (a), (b), (c) or (f)    -   in which    -   L represents oxygen or sulphur,    -   M represents oxygen or sulphur and    -   E represents an ammonium ion,

-   R¹ very particularly preferably represents C₁-C₆-alkyl,    C₂-C₁₇-alkenyl, C₁-C₂-alkoxy-C₁-alkyl, C₁-C₂-alkylthio-C₁-alkyl or    represents cyclopropyl or cyclohexyl, each of which is optionally    monosubstituted by fluorine, chlorine, methyl or methoxy,    -   represents phenyl which is optionally monosubstituted by        fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy,        trifluoromethyl or trifluoromethoxy,

-   R² very particularly preferably represents C₁-C₈-alkyl,    C₂-C₆-alkenyl or C₁-C₄-alkoxy-C₂-C₃-alkyl, phenyl or benzyl, each of    which is optionally monosubstituted by fluorine,

-   R³ very particularly preferably represents C₁-C₈-alkyl.

-   J notably represents trifluoromethoxy,

-   X notably represents hydrogen, chlorine, bromine, methyl, ethyl or    methoxy,

-   Y notably represents hydrogen, chlorine, bromine, methyl or methoxy,    with the proviso, that at least one of the radicals J, X and Y is    located in the 2-position of the phenyl radical and is not hydrogen.

Here, the radicals J, X and Y, having their very particularly preferredmeanings, are notably arranged in the phenyl substitution patterns below

-   A notably represents C₁-C₄-alkyl or cyclopropyl,-   B notably represents hydrogen or methyl,-   A, B and the carbon atom to which they are attached notably    represent saturated C₅-C₆-cycloalkyl in which optionally one ring    member is replaced by oxygen and which is optionally monosubstituted    by methoxymethyl, methoxy, ethoxy, propoxy or butoxy,    or represent

-   D notably represents hydrogen or cyclopropyl,    or-   A and D together notably represent C₃-C₅-alkanediyl,-   G notably represents hydrogen (a) or represents one of the groups

-   R¹ notably represents C₁-C₆-alkyl,-   R² notably represents C₁-C₈-alkyl or benzyl.

The general or preferred radical definitions or illustrations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to precursors andintermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Noteworthiness in accordance with the invention is accorded to thecompounds of the formula (I) in which there is a combination of thedefinitions set out above as being notable.

Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkanediylor alkenyl, can in each case be straight-chain or branched as far asthis is possible, including in combination with heteroatoms, such as,for example, in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted unlessindicated otherwise, and in the case of multiple substitutions thesubstituents can be identical or different.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be specificallymentioned:

TABLE 1 2-OCF₃; X═H; Y═H. A B D CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H HC₄H₉ H H i-C₄H₉ H H s-C₄H₉ H H t-C₄H₉ H H CH₃ CH₃ H C₂H₅ CH₃ H C₃H₇ CH₃H i-C₃H₇ CH₃ H C₄H₉ CH₃ H i-C₄H₉ CH₃ H s-C₄H₉ CH₃ H t-C₄H₉ CH₃ H C₂H₅C₂H₅ H C₃H₇ C₃H₇ H

CH₃ H

CH₃ H

CH₃ H —(CH₂)₂— H —(CH₂)₄— H —(CH₂)₅— H —(CH₂)₆— H —(CH₂)₇— H—(CH₂)₂—O—(CH₂)₂— H —CH₂—O—(CH₂)₃— H —(CH₂)₂—S—(CH₂)₂— H—CH₂—CHCH₃—(CH₂)₃— H —(CH₂)₂—CHCH₃—(CH₂)₂— H —(CH₂)₂—CHC₂H₅—(CH₂)₂— H—(CH₂)₂—CHC₃H₇—(CH₂)₂— H —(CH₂)₂—CHi-C₃H₇—(CH₂)₂— H —CH₂—CHOCH₃—(CH₂)₃—H —CH₂—CHOC₂H₅—(CH₂)₃— H CH₂—CHOC₃H₇—(CH₂)₃— H —CH₂—CHOC₄H₉—(CH₂)₃— H—CH₂—CHO—(CH₂)₂—OCH₃—(CH₂)₃— H —CH₂—CH(O—CH₂)—(CH₂)₃—

H —(CH₂)₂—CHOCH₃—(CH₂)₂— H —(CH₂)₂—CHOC₂H₅—(CH₂)₂- H—(CH₂)₂—CHOC₃H₇—(CH₂)₂— H —(CH₂)₂—CHO-i-C₃H₇—(CH₂)₂— H—CH₂—CH(CH₂—OCH₃)—(CH₂)₃— H —CH₂—CH(CH₂—CH₂—OCH₃)—(CH₂)₃— H—(CH₂)₂—CH(CH₂—OCH₃)—(CH₂)₂— H —(CH₂)₂—CH(CH₂—CH₂—OCH₃)—(CH₂)₂— H—(CH₂)₂—C(CH₃)₂—(CH₂)₂— H —CH₂—(CHCH₃)₂—(CH₂)₂— H

H

H

H

H

H A D B —(CH₂)₃— H —(CH₂)₄— H —CH₂—CHCH₃—CH₂— H —CH₂—CH₂—CHCH₃— H—CH₂—CHCH₃—CHCH₃— H —CH₂—CH(OCH₃)—CH₂— H —CH₂—CH═CH—CH₂— H

H —CH₂—S—CH₂— H —CH₂—S—(CH₂)₂— H —(CH₂)₂—S—CH₂— H

H H CH₃ H H C₂H₅ H H C₃H₇ H H i-C₃H₇ H H

H H

H H

H CH₃ CH₃ H CH₃ C₂H₅ H CH₃ C₃H₇ H CH₃ i-C₃H₇ H CH₃

H CH₃

H CH₃

H

H C₂H₅ CH₃ H C₂H₅ C₂H₅ HTable 2:

-   -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=4-CH₃; Y=H        Table 3:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-CH₃; Y=H.        Table 4:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-C₂H₅; Y=H.        Table 5:    -   A, B and D as Stated in Table 1    -   X=2-CH₃; Y=H; J=5-OCF₃.        Table 6:    -   A, B and D as Stated in Table 1    -   X=2-CH₃; Y=4-CH₃; J=5-OCF₃.        Table 7:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=4-CH₃; Y=6-CH₃.        Table 8:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-C₂H₅; Y=4-CH₃.        Table 9:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-CH₃; Y=4-Cl.        Table 10:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-C₂H₅; Y=4-Cl.        Table 11:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-Cl; Y=4-CH₃.        Table 12:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=5-CH₃; Y=4-CH₃.        Table 13:    -   A, B and D as Stated in Table 1    -   X=2-CH₃; J=4-OCF₃; Y=6-CH₃.        Table 14:    -   A, B and D as Stated in Table 1    -   X=2-C₂H₅; J=4-OCF₃; Y=6-CH₃.        Table 15:    -   A, B and D as Stated in Table 1    -   X=2-C₂H₅; J=4-OCF₃; Y=6-C₂H₅.        Table 16:    -   A, B and D as Stated in Table 1    -   X=2-Cl; J=4-OCF₃; Y=6-CH₃.        Table 17:    -   A, B and D as Stated in Table 1    -   X=2-Cl; J=4-OCF₃; Y=6-C₂H₅.        Table 18:    -   A, B and D as Stated in Table 1    -   X=2-Cl; J=4-OCF₃; Y=H.        Table 19:    -   A, B and D as Stated in Table 1    -   X=2-Br; J=4-OCF₃; Y=H.        Table 20:    -   A, B and D as Stated in Table 1    -   X=2-OCH₃; J=4-OCF₃; Y=6-Cl.        Table 21:    -   A, B and D as Stated in Table 1    -   X=2-OCH₃; J=6-OCF₃; Y=4-Cl.        Table 22:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-Cl; Y=4-Cl.        Table 23:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-Cl; Y=4-Br.        Table 24:    -   A, B and D as Stated in Table 1    -   J=2-OCF₃; X=6-Br; Y=4-Br.        Table 25:    -   A, B and D as Stated in Table 1    -   J=4-OCF₃; X=2-Cl; Y=6-Cl.        Table 26:    -   A, B and D as Stated in Table 1    -   J=4-OCF₃; X=2-Br; Y=6-Cl.        Table 27:    -   A, B and D as Stated in Table 1    -   X=2-Br; J=4-OCF₃; Y=6-Br.        Table 28:    -   A, B and D as Stated in Table 1    -   X=2-Cl; J=5-OCF₃; Y=H.        Table 29:    -   A, B and D as Stated in Table 1    -   X=2-Br; J=5-OCF₃; Y=H.        Table 30:    -   A, B and D as Stated in Table 1    -   X=H; J=2-OCF₃; Y=5-CH₃.

Preferred meanings of the groups listed above in connection with thecrop plant compatibility-improving compounds (“herbicide safeners”) ofthe formulae (IIa), (IIb), (IIc), (IId) and (IIe) are defined below.

-   m preferably represents the numbers 0, 1, 2, 3 or 4.-   A¹ preferably represents one of the divalent heterocyclic groupings    shown below

-   n preferably represents the numbers 0, 1, 2, 3 or 4.-   A² preferably represents in each case optionally methyl-, ethyl-,    methoxycarbonyl- or ethoxycarbonyl-substituted methylene or    ethylene.-   R¹⁴ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino.-   R¹⁵ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy,    allyloxy, 1-allyloxymethylethoxy, methylthio, ethylthio, n- or    i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n-    or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or    diethylamino.-   R¹⁶ preferably represents in each case optionally fluorine-,    chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.-   R¹⁷ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.-   R¹⁸ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together    with R¹⁷ represents one of the radicals —CH₂—O—CH₂—CH₂— and    —CH₂—CH₂—O—CH₂—CH₂— which are optionally substituted by methyl,    ethyl, furyl, phenyl, a fused benzene ring or by two substituents    which, together with the C atom to which they are attached, form a    5- or 6-membered carbocycle.-   R¹⁹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl,    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.-   R²⁰ preferably represents hydrogen, optionally hydroxyl-, cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.-   R²¹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or    phenyl.-   X¹ preferably represents nitro, cyano, fluorine, chlorine, bromine,    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chloro-difluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X² preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X³ preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   t preferably represents the numbers 0, 1, 2, 3 or 4.-   v preferably represents the numbers 0, 1, 2 or 3.-   R²² preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²³ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²⁴ preferably represents hydrogen, in each case optionally cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino, or in each case    optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,    n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,    cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,    cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,    cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino    or cyclohexylamino.-   R²⁵ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, or in    each case optionally cyano-, fluorine-, chlorine-, bromine-,    methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl.-   R²⁶ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, in each    case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-,    ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or    t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally methyl- or    ethyl-substituted butane-1,4-diyl(trimethylene), pentane-1,5-diyl,    1-oxabutane-1,4-diyl or 3-oxapentane-1,5-diyl.-   X⁴ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.-   X⁵ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.

Examples of the compounds of the formula (IIa) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

Table: Examples of the Compounds of the Formula (IIa)

(IIa)

Example (Positions) No. (X¹)_(m) A¹ R¹⁴ IIa-1 (2) Cl, (4) Cl

OCH₃ IIa-2 (2) Cl, (4) Cl

OCH₃ IIa-3 (2) Cl, (4) Cl

OC₂H₅ IIa-4 (2) Cl, (4) Cl

OC₂H₅ IIa-5 (2) Cl

OCH₃ IIa-6 (2) Cl, (4) Cl

OCH₃ IIa-7 (2) F

OCH₃ IIa-8 (2) F

OCH₃ IIa-9 (2) Cl, (4) Cl

OC₂H₅ IIa-10 (2) Cl, (4) CF₃

OCH₃ IIa-11 (2) Cl

OCH₃ IIa-12 —

OC₂H₅ IIa-13 (2) Cl, (4) Cl

OC₂H₅ IIa-14 (2) Cl, (4) Cl

OC₂H₅ IIa-15 (2) Cl, (4) Cl

OC₂H₅ IIa-16 (2) Cl, (4) Cl

OC₂H₅ IIa-17 (2) Cl, (4) Cl

OC₂H₅ IIa-18 —

OH

Examples of the compounds of the formula (IIb) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

Table: Examples of the Compounds of the Formula (IIb)

Example (Position) (Position) No. X² X³ A² R¹⁵ IIb-1 (5) Cl — CH₂ OHIIb-2 (5) Cl — CH₂ OCH₃ IIb-3 (5) Cl — CH₂ OC₂H₅ IIb-4 (5) Cl — CH₂OC₃H₇-n IIb-5 (5) Cl — CH₂ OC₃H₇-i IIb-6 (5) Cl — CH₂ OC₄H₉-n IIb-7 (5)Cl — CH₂ OCH(CH₃)C₅H₁₁-n IIb-8 (5) Cl (2) F CH₂ OH IIb-9 (5) Cl (2) ClCH₂ OH IIb-10 (5) Cl — CH₂ OCH₂CH═CH₂ IIb-11 (5) Cl — CH₂ OC₄H₉-i IIb-12(5) Cl — CH₂

IIb-13 (5) Cl —

OCH₂CH═CH₂ IIb-14 (5) Cl —

OC₂H₅ IIb-15 (5) Cl —

OCH₃

Examples of the compounds of the formula (IIc) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

Table: Examples of the Compounds of the Formula (IIc)

Example No. R¹⁶ N(R¹⁷, R¹⁸) IIc-1 CHCl₂ N(CH₂CH═CH₂)₂ IIc-2 CHCl₂

IIc-3 CHCl₂

IIc-4 CHCl₂

IIc-5 CHCl₂

IIc-6 CHCl₂

IIc-7 CHCl₂

Examples of the compounds of the formula (IId) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

Table: Examples of the Compounds of the Formula (IId)

Example (Positions) (Positions) No. R²² R²³ R²⁴ (X⁴)_(t) (X⁵)_(v) IId-1H H CH₃ (2) OCH₃ — IId-2 H H C₂H₅ (2) OCH₃ — IId-3 H H C₃H₇-n (2) OCH₃ —IId-4 H H C₃H₇-i (2) OCH₃ — IId-5 H H

(2) OCH₃ — IId-6 H H CH₃ (2) OCH₃ — (5) CH₃ IId-7 H H C₂H₅ (2) OCH₃ —(5) CH₃ IId-8 H H C₃H₇-n (2) OCH₃ — (5) CH₃ IId-9 H H C₃H₇-i (2) OCH₃ —(5) CH₃ IId-10 H H

(2) OCH₃ (5) CH₃ — IId-11 H H OCH₃ (2) OCH₃ — (5) CH₃ IId-12 H H OC₂H₅(2) OCH₃ — (5) CH₃ IId-13 H H OC₃H₇-i (2) OCH₃ — (5) CH₃ IId-14 H H SCH₃(2) OCH₃ — (5) CH₃ IId-15 H H SC₂H₅ (2) OCH₃ — (5) CH₃ IId-16 H HSC₃H₇-i (2) OCH₃ — (5) CH₃ IId-17 H H NHCH₃ (2) OCH₃ — (5) CH₃ IId-18 HH NHC₂H₅ (2) OCH₃ — (5) CH₃ IId-19 H H NHC₃H₇-i (2) OCH₃ — (5) CH₃IId-20 H H

(2) OCH₃ (5) CH₃ — IId-21 H H NHCH₃ (2) OCH₃ — IId-22 H H NHC₃H₇-i (2)OCH₃ — IId-23 H H N(CH₃)₂ (2) OCH₃ — IId-24 H H N(CH₃)₂ (3) CH₃ — (4)CH₃ IId-25 H H CH₂—O—CH₃ (2) OCH₃ —

Examples of the compounds of the formula (IIe) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

Table: Examples of the Compounds of the Formula (IIe)

Example (Positions) (Positions) No. R²² R²⁵ R²⁶ (X⁴)_(t) (X⁵)_(v) IIe-1H H CH₃ (2) OCH₃ — IIe-2 H H C₂H₅ (2) OCH₃ — IIe-3 H H C₃H₇-n (2) OCH₃ —IIe-4 H H C₃H₇-i (2) OCH₃ — IIe-5 H H

(2) OCH₃ — IIe-6 H CH₃ CH₃ (2) OCH₃ — IIe-7 H H CH₃ (2) OCH₃ — (5) CH₃IIe-8 H H C₂H₅ (2) OCH₃ — (5) CH₃ IIe-9 H H C₃H₇-n (2) OCH₃ — (5) CH₃IIe-10 H H C₃H₇-i (2) OCH₃ — (5) CH₃ IIe-11 H H

(2) OCH₃ (5) CH₃ — IIe-12 H CH₃ CH₃ (2) OCH₃ — (5) CH₃

Most preferred as crop plant compatibility-improving compound [component(b′)] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dimepiperateand the compounds IIe-5 and IIe-11, and particular emphasis is given tocloquintocet-mexyl and mefenpyr-diethyl.

The compounds of the general formula (IIa) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. WO-A-91/07874, WO-A-95/07897).

The compounds of the general formula (IIb) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. EP-A-191736).

The compounds of the general formula (IIc) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-2218097, DE-A-2350547).

The compounds of the general formula (IId) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680).

The compounds of the general formula (IIe) to be used as safenersaccording to the invention are known and can be prepared by processesknown per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).

Examples of the selective herbicidal combinations according to theinvention comprising in each case one active compound of the formula (I)and one of the safeners defined above are listed in the table below.

Table: Examples of Combinations According to the Invention

Active compounds of the formula (I) Safener I-a cloquintocet-mexyl I-afenchlorazole-ethyl I-a isoxadifen-ethyl I-a mefenpyr-diethyl I-afurilazole I-a fenclorim I-a cumyluron I-a daimuron/dymron I-adimepiperate I-a IIe-11 I-a IIe-5 I-b cloquintocet-mexyl I-bfenchlorazole-ethyl I-b isoxadifen-ethyl I-b mefenpyr-diethyl I-bfurilazole I-b fenclorim I-b cumyluron I-b daimuron/dymron I-bdimepiperate I-b IIe-11 I-b IIe-5 I-c cloquintocet-mexyl I-cfenchlorazole-ethyl I-c isoxadifen-ethyl I-c mefenpyr-diethyl I-cfurilazole I-c fenclorim I-c cumyluron I-c daimuron/dymron I-cdimepiperate I-c IIe-5 I-c IIe-11 I-d cloquintocet-mexyl I-dfenchlorazole-ethyl I-d isoxadifen-ethyl I-d mefenpyr-diethyl I-dfurilazole I-d fenclorim I-d cumyluron I-d daimuron/dymron I-ddimepiperate I-d IIe-11 I-d IIe-5 I-e cloquintocet-mexyl I-efenchlorazole-ethyl I-e isoxadifen-ethyl I-e mefenpyr-diethyl I-efurilazole I-e fenclorim I-e cumyluron I-e daimuron/dymron I-edimepiperate I-e IIe-5 I-e IIe-11 I-f cloquintocet-mexyl I-ffenchlorazole-ethyl I-f isoxadifen-ethyl I-f mefenpyr-diethyl I-ffurilazole I-f fenclorim I-f cumyluron I-f daimuron/dymron I-fdimepiperate I-f IIe-5 I-f IIe-11 I-g cloquintocet-mexyl I-gfenchlorazole-ethyl I-g isoxadifen-ethyl I-g mefenpyr-diethyl I-gfurilazole I-g fenclorim I-g cumyluron I-g daimuron/dymron I-gdimepiperate I-g IIe-5 I-g IIe-11 I-h cloquintocet-mexyl I-hfenchlorazole-ethyl I-h isoxadifen-ethyl I-h mefenpyr-diethyl I-hfurilazole I-h fenclorim I-h cumyluron I-h daimuron/dymron I-hdimepiperate I-h IIe-5 I-h IIe-11

Surprisingly, it has now been found that the active compoundcombinations, defined above, of trifluoromethoxyphenyl-substitutedtetramic acid derivatives of the general formula (I) and safeners(antidotes) from group (b′) listed above, while being very welltolerated by useful plants, have a particularly high herbicidal activityand can be used in various crops, in particular in cereals (especiallywheat), but also in soya beans, potatoes, maize and rice, for theselective control of weeds.

Here, it has to be considered surprising that, from a large number ofknown safeners or antidotes capable of antagonizing the harmful effectof a herbicide on crop plants, those suitable are in particular thecompounds of group (b′) listed above which eliminate the harmful effectof substituted tetramic acid derivatives on the crop plants virtuallycompletely without having a major adverse effect on the herbicidalactivity against the weeds.

Emphasis may be given here to the particularly advantageous effect ofthe particularly and most preferred combination partners from group(b′), in particular with respect to sparing cereal plants, such as, forexample, wheat, barley and rye, but also maize and rice, as crop plants.

In the literature it has already been described how the action ofvarious active compounds can be boosted by addition of ammonium salts.The salts in question, however, are detersive salts (for example WO95/017817) or salts which have relatively long alkyl substituents and/oraryl substituents and which have a permeabilizing action or whichincrease the active compound's solubility (for example EP-A 0 453 086,EP-A 0 664 081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No.5,462,912, U.S. Pat. No. 5,538,937, U.S. Ser. No. 03/0224939, U.S. Ser.No. 05/0009880, U.S. Ser. No. 05/0096386). Moreover, the prior artdescribes the action only for particular active compounds and/orparticular applications of the corresponding compositions. In othercases, in turn, the salts in question are those of sulphonic acids,where the acids themselves have a paralytic action on insects (U.S. Pat.No. 2,842,476). A boost to action by ammonium sulphate, for example, isdescribed by way of example for the herbicides glyphosate,phosphinothricin and certain cyclic ketoenols (U.S. Pat. No. 6,645,914,EP-A2 0 036 106, WO 07/068,427). A corresponding action in the case ofinsecticides is described for certain cyclic ketoenols in WO 07/068,428.

The use of ammonium sulphate as a formulating assistant has also beendescribed for certain active compounds and applications (WO 92/16108),but its purpose therein is to stabilize the formulation, not to boostthe action.

It has now been found, surprisingly, that the action of insecticidesand/or acaricides and/or herbicides from the class of thetrifluoromethoxyphenyl-substituted tetramic acid derivatives of theformula (I) can be boosted significantly through the addition ofammonium salts or phosphonium salts to the application solution orthrough the incorporation of these salts into a formulation comprisingtrifluoromethoxyphenyl-substituted tetramic acid derivatives of theformula (I). The present invention therefore provides for the use ofammonium salts or phosphonium salts for boosting the action of cropprotection compositions which comprise as their active compoundherbicidal and/or insecticidal and/or acaricidaltrifluoromethoxyphenyl-substituted tetramic acid derivatives of theformula (I). The invention likewise provides compositions which compriseherbicidal and/or acaricidal and/or insecticidaltrifluoromethoxyphenyl-substituted tetramic acid derivatives of theformula (I) and action-boosting ammonium salts or phosphonium salts,including not only formulated active compounds but also ready-to-usecompositions (spray liquors). The invention further provides, finally,for the use of these compositions for controlling insect pests and/orspider mites and/or unwanted plant growth.

The compounds of the formula (I) possess a broad insecticidal and/oracaricidal and/or herbicidal activity, but in specific cases theactivity and/or plant tolerance leaves something to be desired. However,some or all of these properties can be improved by adding ammonium saltsor phosphonium salts.

The active compounds can be used in the compositions according to theinvention in a broad concentration range. The concentration of theactive compounds in the formulation is typically 0.1%-50% by weight.

The formula (III′) provides a definition of the ammonium salts andphosphonium salts which, according to the invention, boost the activityof crop protection compositions comprising an active compound from theclass of the trifluoromethoxyphenyl-substituted tetramic acidderivatives of the formula (I)

in which

-   D represents nitrogen or phosphorus,-   D preferably represents nitrogen,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another represent    hydrogen or in each case optionally substituted C₁-C₈-alkyl or mono-    or polyunsaturated, optionally substituted C₁-C₈-alkylene, the    substituents being selectable from halogen, nitro and cyano,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another preferably    represent hydrogen or in each case optionally substituted    C₁-C₄-alkyl, the substituents being selectable from halogen, nitro    and cyano,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another particularly    preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl, sec-butyl or tert-butyl,-   R²⁶, R²⁷, R²⁸ and R²⁹ very particularly preferably represent    hydrogen,-   n represents 1, 2, 3 or 4,-   n preferably represents 1 or 2,-   R³⁰ represents an organic or inorganic anion,-   R³⁰ preferably represents hydrogencarbonate, tetraborate, fluoride,    bromide, iodide, chloride, monohydrogenphosphate,    dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate,    thiosulphate, thiocyanate, formate, lactate, acetate, propionate,    butyrate, pentanoate or oxalate,-   R³⁰ particularly preferably represents lactate, sulphate, nitrate,    thiosulphate, thiocyanate, oxalate or formate.-   R³⁰ very particularly preferably represents sulphate.

Inventively emphasized combinations of active compound, salt andpenetrant are listed in the table below. “Penetrant as per test” meanshere that any compound that acts as a penetrant in the cuticlepenetration test (Baur et al., 1997, Pesticide Science 51, 131-152) issuitable.

The ammonium salts and phosphonium salts of the formula (III′) can beused in a broad concentration range to boost the activity of cropprotection compositions comprising trifluoromethoxyphenyl-substitutedtetramic acid derivatives of the formula (I). In general the ammoniumsalts or phosphonium salts are used in the ready-to-use crop protectioncomposition in a concentration of 0.5 to 80 mmol/l, preferably 0.75 to37.5 mmol/l, more preferably 1.5 to 25 mmol/l. In the case of aformulated product the ammonium salt and/or phosphonium saltconcentration in the formulation is chosen such that it is within thesestated general, preferred or particularly preferred ranges after theformulation has been diluted to the desired active compoundconcentration. The concentration of the salt in the formulation istypically 1%-50% by weight.

In one preferred embodiment of the invention the activity is boosted byadding to the crop protection compositions not only an ammonium saltand/or phosphonium salt but also, additionally, a penetrant. It isconsidered entirely surprising that even in these cases an even greaterboost to activity is observed. The present invention therefore likewiseprovides for the use of a combination of penetrant and ammonium saltsand/or phosphonium salts to boost the activity of crop protectioncompositions which comprise insecticidaltrifluoromethoxyphenyl-substituted tetramic acid derivatives of theformula (I) as active compound. The invention likewise providescompositions which comprise herbicidal and/or acaricidal and/orinsecticidal trifluoromethoxyphenyl-substituted tetramic acidderivatives of the formula (I), penetrants and ammonium salts and/orphosphonium salts, including specifically not only formulated activecompounds but also ready-to-use compositions (spray liquors). Theinvention additionally provides, finally, for the use of thesecompositions for controlling harmful insects and/or spider mites.

In the present context, suitable penetrants are all those substanceswhich are usually employed to improve penetration of agrochemicallyactive compounds into plants. In this context, penetrants are defined inthat they penetrate from the aqueous spray liquor and/or the spraycoating into the cuticles of the plant, thus increasing the mobility ofactive compounds in the cuticles. The method described in the literature(Baur et al., 1997, Pesticide Science 51, 131-152) can be used fordetermining this property.

Examples of suitable penetrants include alkanol alkoxylates. Penetrantsof the invention are alkanol alkoxylates of the formula (IV′)R—O—(-AO)_(v)—R′  (IV′)in which

-   -   R is linear or branched alkyl having 4 to 20 carbon atoms,    -   R′ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,        isobutyl, tert-butyl, n-pentyl or n-hexyl,    -   AO is an ethylene oxide radical, a propylene oxide radical, a        butylene oxide radical or is mixtures of ethylene oxide and        propylene oxide radicals or butylene oxide radicals, and    -   v is a number from 2 to 30.

One preferred group of penetrants are alkanol alkoxylates of the formulaR—O—(-EO—)_(n)—R′  (IV′-a)in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—, and    -   n is a number from 2 to 20.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(-EO—)_(p)—(—PO—)_(q)—R′  (IV′-b)in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—,    -   PO is

-   -   p is a number from 1 to 10, and    -   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(—PO—)_(r)-(EO—)_(S)—R′  (IV′-c)in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—,    -   PO is

-   -   r is a number from 1 to 10, and    -   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(-EO-)_(p)—(-EO—)_(q)—R′  (IV′-d)in which

-   -   R and R′ are as defined above,    -   EO is CH₂—CH₂—O—,    -   BO is

-   -   p is a number from 1 to 10 and    -   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(—BO—)_(r)—(-EO—)_(s)—R′  (IV′-e)in which

-   -   R and R′ are as defined above,    -   BO is

-   -   EO is CH₂—CH₂—O—,    -   r is a number from 1 to 10 and    -   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaCH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—R′  (IV′-f)in which

-   -   R′ is as defined above,    -   t is a number from 8 to 13,    -   u is a number from 6 to 17.

In the formulae indicated above,

-   R is preferably butyl, isobutyl, n-pentyl, isopentyl, neopentyl,    n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl,    decyl, n-dodecyl, isododecyl, lauryl, myristyl, isotridecyl,    trimethylnonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (IV′-c) mentionmay be made of 2-ethylhexyl alkoxylate of the formula

in which

-   -   EO is —CH₂—CH₂—O—,    -   PO is

andthe numbers 8 and 6 represent average values.

As an example of an alkanol alkoxylate of the formula (IV′-d) mentionmay be made of the formulaCH₃—(CH₂)₁₀—O—(-EO—)₆—(—BO—)₂—CH₃  (IV′-d-1)in which

-   -   EO is CH₂—CH₂—O—,    -   BO is

and

-   -   the numbers 10, 6 and 2 represent average values.

Particularly preferred alkanol alkoxylates of the formula (IV′-f) arecompounds of this formula in which

-   -   t is a number from 9 to 12 and    -   u is a number from 7 to 9.

Mention may be made with very particular preference of alkanolalkoxylate of the formula (IV′-f-1)CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—H  (IV′-f-1)in which

-   -   t stands for the average value 10.5 and    -   u stands for the average value 8.4.

A general definition of the alkanol alkoxylates is given by the formulaeabove. These substances are mixtures of compounds of the stated typewith different chain lengths. The indices therefore have average valueswhich may also deviate from whole numbers.

The alkanol alkoxylates of the formulae stated are known and in somecases are available commercially or can be prepared by known methods(cf. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Suitable penetrants also include, for example, substances which promotethe availability of the compounds of the formula (I) in the spraycoating. These include, for example, mineral or vegetable oils. Suitableoils are all mineral or vegetable oils—modified or otherwise—which cantypically be used in agrochemical compositions. Mention may be made byway of example of sunflower oil, rapeseed oil, olive oil, castor oil,colza oil, maize seed oil, cotton seed oil and soya bean oil, or theesters of said oils. Preference is given to rapeseed oil, sunflower oiland their methyl or ethyl esters.

The concentration of penetrant in the compositions of the invention canbe varied within a wide range. In the case of a formulated cropprotection composition it is in general 1% to 95%, preferably 1% to 55%,more preferably 15%-40% by weight. In the ready-to-use compositions(spray liquors) the concentrations are generally between 0.1 and 10 g/l,preferably between 0.5 and 5 g/l.

Crop protection compositions of the invention may also comprise furthercomponents, examples being surfactants and/or dispersing assistants oremulsifiers.

Suitable nonionic surfactants and/or dispersing assistants include allsubstances of this type that can typically be used in agrochemicalcompositions. Preferably mention may be made of polyethyleneoxide-polypropylene oxide block copolymers, polyethylene glycol ethersof linear alcohols, reaction products of fatty acids with ethylene oxideand/or propylene oxide, and also polyvinyl alcohol,polyvinylpyrrolidone, copolymers of polyvinyl alcohol andpolyvinylpyrrolidone, and copolymers of (meth)acrylic acid and(meth)acrylic esters, and additionally alkyl ethoxylates and alkylarylethoxylates, which optionally may be phosphated and optionally may beneutralized with bases, mention being made, by way of example, ofsorbitol ethoxylates, and, as well, polyoxyalkylenamine derivatives.

Suitable anionic surfactants include all substances of this type thatcan typically be used in agrochemical compositions. Preference is givento alkali metal salts and alkaline earth metal salts of alkylsulphonicacids or alkylarylsulphonic acids.

A further preferred group of anionic surfactants and/or dispersingassistants are the following salts that are of low solubility in plantoil: salts of polystyrenesulphonic acids, salts of polyvinylsulphonicacids, salts of naphthalenesulphonic acid-formaldehyde condensationproducts, salts of condensation products of naphthalenesulphonic acid,phenolsulphonic acid and formaldehyde, and salts of lignosulphonic acid.

Suitable additives which may be included in the formulations of theinvention are emulsifiers, foam inhibitors, preservatives, antioxidants,colorants and inert filling materials.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products ofalkylphenols with ethylene oxide and/or propylene oxide, ethoxylatedarylalkylphenols, and also ethoxylated and propoxylatedarylalkylphenols, and also sulphated or phosphated arylalkyl ethoxylatesand/or arylalkyl ethoxypropoxylates, mention being made by way ofexample of sorbitan derivatives, such as polyethylene oxide-sorbitanfatty acid esters, and sorbitan fatty acid esters.

Using, for example, according to process (A) ethylN-(2,6-dichloro-4-trifluoromethoxyphenyl-acetyl)-1-aminocyclohexanecarboxylateas starting material, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, for example, according to process (Bα)3-(2-chloro-4-trifluoromethoxy-6-methoxyphenyl)-5,5-dimethylpyrrolidine-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (Bβ)3-(2,6-dibromo-4-trifluoromethoxyphenyl)-5,5-dimethylpyrrolidine-2,4-dioneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (C)8-[(2,6-dichloro-4-trifluoromethoxy)phenyl]-1-aza-bicyclo-(4,3,0^(1,6))-nonane-7,9-dioneand ethyl chloroformate as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (D)3-(2,6-dibromo-4-trifluoromethoxyphenyl)-5,5-dimethyl-6-pyrrolidine-2,4-dioneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using, for example, according to process (E)3-(2,6-dichloro-4-trifluoromethoxyphenyl)-5,5-pentamethylenepyrrolidine-2,4-dioneand methanesulphonyl chloride as starting material, the course of thereaction can be represented by the reaction scheme below:

Using, for example, according to process (F)3-(2-trifluoromethoxyphenyl)-5,5-dimethylpyrrolidine-2,4-dione and2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by the reactionscheme below:

Using, for example, according to process (G)3-(2-chloro-4-trifluoromethoxy-6-methoxyphenyl]-5-cyclopropyl-5-methylpyrrolidine-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, for example, according to process (H) variant α3-(2,6-dibromo-4-trifluoromethoxyphenyl)-5,5-tetramethylenepyrrolidine-2,4-dioneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the reaction scheme below:

Using, for example, according to process (H) variant β3-(2,6-dichloro-4-trifluoromethoxyphenyl)-5,5-dimethylpyrrolidine-2,4-dioneand dimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the scheme below:

The compounds, required as starting materials in the process (A)according to the invention, of the formula (II)

in whichA, B, D, J, X, Y and R⁸ have the meanings given above,are novel.

The acylamino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XIII)

in whichA, B, R⁸ and D have the meanings given above,are acylated with substituted phenylacetic acid derivatives of theformula (XIV)

in which

-   J, X and Y have the meanings given above and-   Z represents a leaving group introduced by reagents for activating    carboxylic acids, such as carbonyldiimidazole, carbonyldiimides    (such as, for example, dicyclohexylcarbodiimide), phosphorylating    reagents (such as, for example, POCl₃, BOP—Cl), halogenating agents,    such as, for example, thionyl chloride, oxalyl chloride, phosgene or    chloroformic esters,-   (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6,    341-5, 1968)    or when acylamino acids of the formula (XV)

in whichA, B, D, J, X and Y have the meanings given above,are esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XV)

in whichA, B, D, J, X and Y have the meanings given above,are novel.

The compounds of the formula (XV) are obtained when amino acids of theformula (XVI)

in whichA, B and D have the meanings given above,are acylated, for example, according to Schotten-Baumann (Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, p. 505) withsubstituted phenylacetic acid derivatives of the formula (XIV)

in whichJ, X and Y have the meanings given above andZ has the meaning given above.

The compounds of the formula (XIV) are novel. They can be obtained bymethods known in principle and as shown in the examples (see, forexample, H. Henecka, Houben-Weyl, Methoden der Organischen Chemie, Vol.8, pp. 467-469 (1952)).

The compounds of the formula (XIV) are obtained, for example, whensubstituted phenylacetic acids of the formula (XVII)

in whichJ, X and Y have the meaning given above,are reacted with halogenating agents (for example thionyl chloride,thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride,phosphorus tribromide or phosphorus pentachloride), phosphonylatingagents (such as, for example, POCl₃, BOP—Cl), carbonyldiimidazole,carbonyldiimides (for example dicyclohexylcarbonyldiimide), optionallyin the presence of a diluent (for example optionally chlorinatedaliphatic or aromatic hydrocarbons such as toluene or methylene chlorideor ethers, for example tetrahydrofuran, dioxane, methyl tert-butylether), at temperatures of from −20° C. to 150° C., preferably from −10°C. to 100° C.

Some of the compounds of the formula (XVII) are commercially available.Novel compounds of the formula (XVII) are described in the experimentalpart or can be prepared by processes known from the applications citedat the outset.

Some of the compounds of the formula (XIII) and (XVI) are known, and/orcan be prepared by known processes (see, for example, Compagnon, MiocqueAnn. Chim. (Paris) [14] 5, pp. 11-22, 23-27 (1970)).

The substituted cyclic aminocarboxylic acids of the formula (XVI) inwhich A and B form a ring can generally be obtained by theBucherer-Bergs synthesis or by the Strecker synthesis, where they are ineach case obtained in different isomeric forms. Thus, the conditions ofthe Bucherer-Bergs synthesis yield predominantly the isomers(hereinbelow, for the sake of simplicity, referred to as β) in which theradicals R and the carboxyl group are in equatorial positions, whereasthe conditions of the Strecker synthesis yield predominantly the isomers(hereinbelow, for the sake of simplicity, referred to as α) in which theamino group and the radicals R are in equatorial positions.

(L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C. Jitrangeri, Can.J. Chem. 53, 3339 (1975)).

Furthermore, the starting materials, employed in the above process (A),of the formula (II)

in whichA, B, D, J, X, Y and R⁸ have the meanings given above,can be prepared by reacting aminonitriles of the formula (XVIII)

in whichA, B and D have the meanings given above,with substituted phenylacetic acid derivatives of the formula (XIV)

in whichJ, X, Y and Z have the meanings given above,to give compounds of the formula (XIX)

in whichA, B, D, J, X and Y have the meanings given above,and then subjecting these to an acidic alcoholysis.

The compounds of the formula (XIX) are likewise novel.

The acid halides of the formula (III), carboxylic anhydrides of theformula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), sulphonyl chlorides of the formula (VII), phosphoruscompounds of the formula (VIII) and metal hydroxides, metal alkoxides oramines of the formulae (IX) and (X), respectively, and isocyanates ofthe formula (XI) and carbamoyl chlorides of the formula (XII)furthermore required as starting materials for carrying out theprocesses (B), (C), (D), (E), (F), (G) and (H) according to theinvention are generally known compounds of organic or inorganicchemistry.

In addition, the compounds of the formulae (XIII), (XVI) and (XVIII) areknown from the patent applications cited at the outset and/or can beprepared by the methods given therein.

The process (A) is characterized in that compounds of the formula (II)in which A, B, D, J, X, Y and R⁸ have the meanings given above aresubjected to an intramolecular condensation in the presence of a base.

Suitable diluents for use in the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, isopropanol,butanol, isobutanol and tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which may also be used in the presenceof phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris(methoxyethoxyethyl)amine). It is furthermore possible to usealkali metals, such as sodium or potassium. Further, it is possible toemploy alkali metal and alkaline earth metal amides and hydrides, suchas sodium amide, sodium hydride and calcium hydride, and additionallyalso alkali metal alkoxides, such as sodium methoxide, sodium ethoxideand potassium tert-butoxide.

When carrying out the process (A) according to the invention, thereaction temperatures may be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in about doubly equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

The process (B-α) is characterized in that compounds of the formula(I-a) are reacted with carbonyl halides of the formula (III), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for use in the process (B-α) according to theinvention are all solvents inert towards the acid halides. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. If the acid halide is sufficiently stable tohydrolysis, the reaction can also be carried out in the presence ofwater.

Suitable acid binders for the reaction according to the process (B-α)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

The reaction temperatures in the process (B-α) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (B-α) according to the invention, thestarting materials of the formula (I-a) and the carbonyl halide of theformula (III) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of the carbonyl halide. Work-up is carried out bycustomary methods.

The process (B-β) is characterized in that compounds of the formula(I-a) are reacted with carboxylic anhydrides of the formula (IV), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for use in the process (B-β) according to theinvention are, preferably, the diluents which are also preferred whenusing acid halides. Besides, excess carboxylic anhydride maysimultaneously act as diluent.

Suitable acid binders, which are added, if appropriate, for process(B-β) are, preferably, the acid binders which are also preferred whenusing acid halides.

The reaction temperatures in the process (B-β) according to theinvention may be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (B-β) according to the invention, thestarting materials of the formula (I-a) and the carboxylic anhydride ofthe formula (IV) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of carboxylic anhydride. Work-up is carried out bycustomary methods.

In general, diluent and excess carboxylic anhydride and the carboxylicacid formed are removed by distillation or by washing with an organicsolvent or with water.

The process (C) is characterized in that compounds of the formula (I-a)are reacted with chloroformic esters or chloroformic thioesters of theformula (V), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Suitable acid binders for the reaction according to the process (C)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethylaniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal and alkaline earth metal carbonates, such assodium carbonate, potassium carbonate and calcium carbonate, and alsoalkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

Suitable diluents for use in the process (C) according to the inventionare all solvents which are inert towards the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzine, benzene, toluene, xylene and tetralin, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe process is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thioester of the formula (V) are generally eachemployed in approximately equivalent amounts. However, it is alsopossible to use a relatively large excess (up to 2 mol) of one componentor the other. Work-up is carried out by customary methods. In general,precipitated salts are removed and the reaction mixture that remains isconcentrated by removing the diluent under reduced pressure.

The process (D) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with compounds of the formula(VI) in the presence of a diluent and, if appropriate, in the presenceof an acid binder.

In preparation process (D), about 1 mol of chloromonothioformic ester orchlorodithioformic ester of the formula (VI) is employed per mole of thestarting material of the formula (I-a) at from 0 to 120° C., preferablyfrom 20 to 60° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides, andalso halogenated alkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents, such as, forexample, sodium hydride or potassium tert-butoxide, the further additionof acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases; sodium hydroxide, sodium carbonate, potassium carbonate, pyridineand triethylamine may be mentioned by way of example.

The reaction may be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (E) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with sulphonyl chlorides ofthe formula (VII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

In preparation process (E), about 1 mol of sulphonyl chloride of theformula (VII) is reacted per mole of the starting material of theformula (I-a) at from −20 to 150° C., preferably from 20 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction may be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (F) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with phosphorus compounds ofthe formula (VIII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

In preparation process (F), to obtain compounds of the formula (I-e),from 1 to 2, preferably from 1 to 1.3, mol of the phosphorus compound ofthe formula (VIII) are reacted per mole of the compounds (I-a), attemperatures between −40° C. and 150° C., preferably between −10 and110° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

Suitable acid binders which are added, if appropriate, are customaryinorganic or organic bases, such as hydroxides, carbonates or amines.Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine may be mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry. Theend products are preferably purified by crystallization, chromatographicpurification or “incipient distillation”, i.e. removal of the volatilecomponents under reduced pressure.

The process (G) is characterized in that compounds of the formula (I-a)are reacted with metal hydroxides or metal alkoxides of the formula (IX)or amines of the formula (X), if appropriate in the presence of adiluent.

Suitable diluents for use in the process (G) according to the inventionare, preferably, ethers, such as tetrahydrofuran, dioxane, diethylether, or else alcohols, such as methanol, ethanol, isopropanol, andalso water.

The process (G) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (H) according to the invention is characterized in thatcompounds of the formula (I-a) are reacted with (H-α) compounds of theformula (XI), if appropriate in the presence of a diluent and ifappropriate in the presence of a catalyst, or (H-β) with compounds ofthe formula (XII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

In preparation process (H-α), about 1 mol of isocyanate of the formula(XI) is reacted per mole of starting material of the formula (I-a), atfrom 0 to 100° C., preferably from 20 to 50° C.

Suitable diluents which are added, if appropriate, are all inert organicsolvents, such as ethers, amides, nitriles, sulphones or sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Suitable for use as catalysts are, very advantageously, organotincompounds, such as, for example, dibutyltin dilaurate. The reaction ispreferably carried out at atmospheric pressure.

In preparation process (H-β), about 1 mol of carbamoyl chloride of theformula (XII) is reacted per mole of starting compound of the formula(I-a), at from −20 to 150° C., preferably at from 0 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides orhalogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The active compounds of the invention, in combination with good planttolerance and favourable toxicity to warm-blooded animals and beingtolerated well by the environment, are suitable for protecting plantsand plant organs, for increasing the harvest yields, for improving thequality of the harvested material and for controlling animal pests, inparticular insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, in animal husbandry, inforests, in gardens and leisure facilities, in the protection of storedproducts and of materials, and in the hygiene sector. They may bepreferably employed as crop protection agents. They are active againstnormally sensitive and resistant species and against all or some stagesof development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscelides obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.,Odontotermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). Ifappropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on the surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspension-emulsion concentrates, naturalmaterials impregnated with active compound, synthetic materialsimpregnated with active compound, fertilizers and microencapsulations inpolymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable plants or else before or during theapplication.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties such as certain technical properties and/or also particularbiological properties. Typical suitable auxiliaries are: extenders,solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

Suitable Solid Carriers are:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example, nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates and also proteinhydrolysates; suitable dispersants are nonionic and/or ionic substances,for example from the classes of the alcohol-POE and/or -POP ethers, acidand/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/orPOP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/orPOP-sorbitan- or -sugar adducts, alkyl or aryl sulphates, alkyl- orarylsulphonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. Furthermore, suitable oligo- or polymers, for examplethose derived from vinylic monomers, from acrylic acid, from EO and/orPO alone or in combination with, for example, (poly)alcohols or(poly)amines. It is also possible to employ lignin and its sulphonicacid derivatives, unmodified and modified celluloses, aromatic and/oraliphatic sulphonic acids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

The formulations generally comprise between 0.01 and 98% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be used in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances, herbicides,safeners, fertilizers or semiochemicals.

Particularly favourable mixing components are, for example, thefollowing compounds:

Fungicides:

Inhibitors of Nucleic Acid Synthesis

-   -   benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,        dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl,        metalaxyl-M, ofurace, oxadixyl, oxolinic acid        Inhibitors of Mitosis and Cell Division    -   benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron,        thiabendazole, thiophanate-methyl, zoxamide        Inhibitors of Respiratory Chain Complex I    -   diflumetorim        Inhibitors of Respiratory Chain Complex II    -   boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil,        oxycarboxin, penthiopyrad, thifluzamide        Inhibitors of Respiratory Chain Complex III    -   azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone,        fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin,        orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin        Decouplers    -   dinocap, fluazinam        Inhibitors of ATP Production    -   fentin acetate, fentin chloride, fentin hydroxide, silthiofam        Inhibitors of Amino Acid Biosynthesis and Protein Biosynthesis    -   andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin        hydrochloride hydrate, mepanipyrim, pyrimethanil        Inhibitors of Signal Transduction    -   fenpiclonil, fludioxonil, quinoxyfen        Inhibitors of Lipid and Membrane Synthesis    -   chlozolinate, iprodione, procymidone, vinclozolin    -   ampropylfos, potassium-ampropylfos, edifenphos, iprobenfos        (IBP), isoprothiolane, pyrazophos    -   tolclofos-methyl, biphenyl    -   iodocarb, propamocarb, propamocarb hydrochloride        Inhibitors of Ergosterol Biosynthesis    -   fenhexamid,    -   azaconazole, bitertanol, bromuconazole, cyproconazole,        diclobutrazole, difenoconazole, diniconazole, diniconazole-M,        epoxiconazole, etaconazole, fenbuconazole, fluquinconazole,        flusilazole, flutriafol, furconazole, furconazole-cis,        hexaconazole, imibenconazole, ipconazole, metconazole,        myclobutanil, paclobutrazole, penconazole, propiconazole,        prothioconazole, simeconazole, tebuconazole, tetraconazole,        triadimefon, triadimenol, triticonazole, uniconazole,        voriconazole, imazalil, imazalil sulphate, oxpoconazole,        fenarimol, flurprimidol, nuarimol, pyrifenox, triforine,        pefurazoate, prochloraz, triflumizole, viniconazole,    -   aldimorph, dodemorph, dodemorph acetate, fenpropimorph,        tridemorph, fenpropidin, spiroxamine,    -   naftifine, pyributicarb, terbinafine        Inhibitors of Cell Wall Synthesis    -   benthiavalicarb, bialaphos, dimethomorph, flumorph,        iprovalicarb, polyoxins, polyoxorim, validamycin A        Inhibitors of Melanin Biosynthesis    -   capropamid, diclocymet, fenoxanil, phthalid, pyroquilon,        tricyclazole        Resistance Inductors    -   acibenzolar-S-methyl, probenazole, tiadinil        Multisite    -   captafol, captan, chlorothalonil, copper salts such as: copper        hydroxide, copper naphthenate, copper oxychloride, copper        sulphate, copper oxide, oxine-copper and Bordeaux mixture,        dichlofluanid, dithianon, dodine, dodine free base, ferbam,        folpet, fluorofolpet, guazatine, guazatine acetate,        iminoctadine, iminoctadine albesilate, iminoctadine triacetate,        mancopper, mancozeb, maneb, metiram, metiram zinc, propineb,        sulphur and sulphur preparations containing calcium        polysulphide, thiram, tolylfluanid, zineb, ziram        Unknown Mechanism    -   amibromdol, benthiazole, bethoxazin, capsimycin, carvone,        chinomethionat, chloropicrin, cufraneb, cyflufenamid, cymoxanil,        dazomet, debacarb, diclomezine, dichlorophen, dicloran,        difenzoquat, difenzoquat methyl sulphate, diphenylamine,        ethaboxam, ferimzone, flumetover, flusulphamide, fluopicolide,        fluoroimide, hexachlorobenzene, 8-hydroxy-quinoline sulphate,        irumamycin, methasulphocarb, metrafenone, methyl isothiocyanate,        mildiomycin, natamycin, nickel dimethyl dithiocarbamate,        nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin,        pentachlorophenol and salts, 2-phenylphenol and salts,        piperalin, propanosine-sodium, proquinazid, pyrrolnitrin,        quintozene, tecloftalam, tecnazene, triazoxide, trichlamide,        zarilamid and 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,        N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulphonamide,        2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,        2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,        3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,        cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,        2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,3-triazol-3-one        (185336-79-2), methyl        1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,        3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl        2-[[[cyclopropyl[(4-methoxyphenyl)imino]methyl]thio]methyl]-.alpha.-(methoxymethylene)benzacetate,        4-chloro-alpha-propynyloxy-N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]benzacet-amide,        (2S)—N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide,        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,        5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,        5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,        N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,        N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloronicotinamide,        2-butoxy-6-iodo-3-propylbenzopyranon-4-one,        N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]-methyl}-2-benzacetamide,        N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide,        2-[[[[1-[3(1-fluoro-2-phenylethyl)oxy]phenyl]ethylidene]amino]oxy]-methyl]-alpha-(methoxyimino)-N-methyl-alphaE-benzacetamide,        N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,        N-(3′,4′-dichloro-5-fluoro-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,        N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide,        1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylic        acid,        O-[1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1H-imidazole-1-carbothioic        acid,        2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide        Bactericides:        bronopol, dichlorophen, nitrapyrin, nickel        dimethyldithiocarbamate, kasugamycin, octhilinone,        furancarboxylic acid, oxytetracycline, probenazole,        streptomycin, tecloftalam, copper sulphate and other copper        preparations.        Insecticides/Acaricides/Nematicides:

Acetylcholine Esterase (AChE) Inhibitors

-   -   carbamates,    -   for example alanycarb, aldicarb, aldoxycarb, allyxycarb,        aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb,        butocarboxim, butoxycarboxim, carbaryl, carbofuran,        carbosulphan, cloethocarb, dimetilan, ethiofencarb, fenobucarb,        fenothiocarb, formetanate, furathiocarb, isoprocarb,        metam-sodium, methiocarb, methomyl, metolcarb, oxamyl,        pirimicarb, promecarb, propoxur, thiodicarb, thiofanox,        trimethacarb, XMC, xylylcarb, triazamate    -   organophosphates,    -   for example acephate, azamethiphos, azinphos (-methyl, -ethyl),        bromophos-ethyl, bromfenvinfos (-methyl), butathiofos,        cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos,        chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos,        cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl,        demeton-S-methylsulphone, dialifos, diazinon, dichlofenthion,        dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,        dioxabenzofos, disulphoton, EPN, ethion, ethoprophos, etrimfos,        famphur, fenamiphos, fenitrothion, fensulphothion, fenthion,        flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate,        heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos,        isopropyl O-salicylate, isoxathion, malathion, mecarbam,        methacrifos, methamidophos, methidathion, mevinphos,        monocrotophos, naled, omethoate, oxydemeton-methyl, parathion        (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet,        phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl),        profenofos, propaphos, propetamphos, prothiofos, prothoate,        pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos,        sulphotep, sulprofos, tebupirimfos, temephos, terbufos,        tetrachlorvinphos, thiometon, triazophos, triclorfon,        vamidothion

Sodium Channel Modulators/Voltage-Dependent Sodium Channel Blockers

-   -   pyrethroids,    -   for example acrinathrin, allethrin (d-cis-trans, d-trans),        beta-cyfluthrin, bifenthrin, bioallethrin,        bioallethrin-S-cyclopentyl isomer, bioethanomethrin,        biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin,        cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin,        cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-,        zeta-), cyphenothrin, deltamethrin, empenthrin (1R isomer),        esfenvalerate, etofenprox, fenfluthrin, fenpropathrin,        fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate,        flufenprox, flumethrin, fluvalinate, fubfenprox,        gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin,        metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans        isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin,        resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin,        terallethrin, tetramethrin (1R isomer), tralomethrin,        transfluthrin, ZXI 8901, pyrethrins (pyrethrum)    -   DDT    -   oxadiazines,    -   for example indoxacarb    -   semicarbazones,    -   for example metaflumizone (BAS3201)

Acetylcholine Receptor Agonists/Antagonists

-   -   chloronicotinyls,    -   for example acetamiprid, clothianidin, dinotefuran,        imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam    -   nicotine, bensultap, cartap

Acetylcholine Receptor Modulators

-   -   spinosyns,    -   for example spinosad

GABA-Controlled Chloride Channel Antagonists

-   -   organochlorines,    -   for example camphechlor, chlordane, endosulphan, gamma-HCH, HCH,        heptachlor, lindane, methoxychlor    -   fiprols,    -   for example acetoprole, ethiprole, fipronil, pyrafluprole,        pyriprole, vaniliprole

Chloride Channel Activators

-   -   mectins,    -   for example abamectin, emamectin, emamectin-benzoate,        ivermectin, lepimectin, milbemycin

Juvenile Hormone Mimetics,

-   -   for example diofenolan, epofenonane, fenoxycarb, hydroprene,        kinoprene, methoprene, pyriproxifen, triprene

Ecdysone Agonists/Disruptors

-   -   diacylhydrazines,    -   for example chromafenozide, halofenozide, methoxyfenozide,        tebufenozide

Chitin Biosynthesis Inhibitors

-   -   benzoylureas,    -   for example bistrifluoron, chlofluazuron, diflubenzuron,        fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,        novaluron, noviflumuron, penfluoron, teflubenzuron, triflumuron    -   buprofezin    -   cyromazine

Oxidative Phosphorylation Inhibitors, ATP Disruptors

-   -   diafenthiuron    -   organotin compounds,    -   for example azocyclotin, cyhexatin, fenbutatin-oxide

Oxidative Phosphorylation Decouplers Acting by Interrupting the H-ProtonGradient

-   -   pyrroles,    -   for example chlorfenapyr    -   dinitrophenols,    -   for example binapacyrl, dinobuton, dinocap, DNOC, meptyldinocap

Site-I Electron Transport Inhibitors

-   -   METI's,    -   for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben,        tebufenpyrad, tolfenpyrad    -   hydramethylnon    -   dicofol

Site-II Electron Transport Inhibitors

-   -   rotenone

Site-III Electron Transport Inhibitors

-   -   acequinocyl, fluacrypyrim

Microbial Disruptors of the Insect Gut Membrane

-   -   Bacillus thuringiensis strains

Lipid Synthesis Inhibitors

-   -   tetronic acids,    -   for example spirodiclofen, spiromesifen    -   tetramic acids,    -   for example spirotetramate,        cis-3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one    -   carboxamides,    -   for example flonicamid    -   octopaminergic agonists,    -   for example amitraz

Inhibitors of Magnesium-Stimulated ATPase,

-   -   propargite    -   nereistoxin analogues,    -   for example thiocyclam hydrogen oxalate, thiosultap-sodium

Ryanodine Receptor Agonists,

-   -   benzodicarboxamides,    -   for example flubendiamide    -   anthranilamides,    -   for example rynaxypyr        (3-bromo-N-{4-chloro-2-methyl-6-[(methylamino)carbonyl]-phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide)

Biologicals, Hormones or Pheromones

-   -   azadirachtin, Bacillus spec., Beauveria spec., codlemone,        Metarrhizium spec., Paecilomyces spec., thuringiensin,        Verticillium spec.

Active Compounds with Unknown or Unspecific Mechanisms of Action

-   -   fumigants,    -   for example aluminium phosphide, methyl bromide, sulphuryl        fluoride    -   antifeedants,    -   for example cryolite, flonicamid, pymetrozine    -   mite growth inhibitors,    -   for example clofentezine, etoxazole, hexythiazox    -   amidoflumet, benclothiaz, benzoximate, bifenazate,        bromopropylate, buprofezin, chinomethionat, chlordimeform,        chlorobenzilate, chloropicrin, clothiazoben, cycloprene,        cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine,        flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure,        metoxadiazone, petroleum, piperonyl butoxide, potassium oleate,        pyridalyl, sulphluramid, tetradifon, tetrasul, triarathene,        verbutin

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents for improving the plant properties, is also possible.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce degradation of the activecompound after use in the environment of the plant, on the surface ofparts of plants or in plant tissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.00000001 to95% by weight of active compound, preferably between 0.00001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. These can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars (obtained by geneticengineering) which are to be treated according to the invention includeall plants which, by virtue of the genetic modification, receivedgenetic material which imparts particular advantageous, useful traits tothese plants. Examples of such traits are better plant growth, increasedtolerance to high or low temperatures, increased tolerance to drought orto water or soil salt content, increased flowering performance, easierharvesting, accelerated maturation, higher harvest yields, higherquality and/or a higher nutritional value of the harvested products,better storage stability and/or processability of the harvestedproducts. Further and particularly emphasized examples of such traitsare a better defense of the plants against animal and microbial pests,such as against insects, mites, phytopathogenic fungi, bacteria and/orviruses, and also increased tolerance of the plants to certainherbicidally active compounds. Examples of transgenic plants which maybe mentioned are the important crop plants, such as cereals (wheat,rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and othervegetable varieties, cotton, tobacco, oilseed rape and also fruit plants(with the fruits apples, pears, citrus fruits and grapes), andparticular emphasis is given to maize, soya beans, potatoes, cotton,tobacco and oilseed rape. Traits that are emphasized are in particularincreased defense of the plants against insects, arachnids, nematodesand slugs and snails by virtue of toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF andalso combinations thereof) (referred to hereinbelow as “Bt plants”).Traits that are also particularly emphasized are the increased defenseof plants against fungi, bacteria and viruses by systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and resistance genesand correspondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance ofplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinothricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinothricin, for example oilseed rape), IMP® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plant cultivars will bedeveloped and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula I and/or the active compound mixtures according to theinvention. The preferred ranges stated above for the active compounds ormixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ecto- and endoparasites), suchas hard ticks, soft ticks, mange mites, leaf mites, flies (biting andlicking), parasitic fly larvae, lice, hair lice, feather lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reductions in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector and in animal husbandry in a known manner by enteraladministration in the form of, for example, tablets, capsules, potions,drenches, granules, pastes, boluses, the feed-through process andsuppositories, by parenteral administration, such as, for example, byinjection (intramuscular, subcutaneous, intravenous, intraperitoneal andthe like), implants, by nasal administration, by dermal use in the form,for example, of dipping or bathing, spraying, pouring on and spottingon, washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100- to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;

Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cardboards, leather, wood and processed wood productsand coating compositions.

The ready-to-use compositions may, if appropriate, comprise furtherinsecticides and, if appropriate, one or more fungicides.

With respect to possible additional additives, reference may be made tothe insecticides and fungicides mentioned above.

The compounds according to the invention can likewise be employed forprotecting objects which come into contact with saltwater or brackishwater, in particular hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Furthermore, the compounds according to the invention, alone or incombinations with other active compounds, may be employed as antifoulingagents.

In domestic, hygiene and stored-product protection, the active compoundsare also suitable for controlling animal pests, in particular insects,arachnids and mites, which are found in enclosed spaces such as, forexample, dwellings, factory halls, offices, vehicle cabins and the like.They can be employed alone or in combination with other active compoundsand auxiliaries in domestic insecticide products for controlling thesepests. They are active against sensitive and resistant species andagainst all developmental stages. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can also be used asdefoliants, desiccants, haulm killers and, in particular, as weedkillers. Weeds in the broadest sense are understood as meaning allplants which grow at locations where they are undesired. Whether thesubstances according to the invention act as nonselective or selectiveherbicides depends essentially on the application rate.

The active compounds according to the invention can be used for examplein the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digi-taria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but extends in the same manner toother plants.

Depending on the concentration, the active compounds according to theinvention are suitable for the nonselective weed control on, forexample, industrial terrains and railway tracks and on paths andlocations with and without trees. Likewise the active compoundsaccording to the invention can be employed for controlling weeds inperennial crops, for example forests, ornamental tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

The active compounds according to the invention have strong herbicidalactivity and a broad activity spectrum when used on the soil and onaerial plant parts. To a certain extent, they are also suitable for theselective control of monocotyledonous and dicotyledonous weeds inmonocotyledonous and dicotyledonous crops, both pre- and post-emergence.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspoemulsion concentrates,natural and synthetic materials impregnated with active compound, andvery fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics, such as xylene, toluene or alkyl-naphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andalso water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates, suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam-formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in theirformulations, can also be used for weed control purposes as a mixturewith known herbicides and/or with substances which improve crop planttolerance (“safeners”), ready mixes or tank mixes being possible.Mixtures with herbicide products which contain one or more knownherbicides and a safener are hence also possible.

Herbicides which are suitable for the mixtures are known herbicides, forexample2-chloro-5-[2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluoro-N-[methyl(1-methylethyl)sulphamoyl]benzamide,acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulphuron,aminopyralid, anilofos, asulam, atrazine, azafenidin, azimsulphuron,beflubutamid, benazolin (-ethyl), bencarbazone, benfuresate,bensulphuron (-methyl), bentazone, benzfendizone, benzobicyclon,benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil(-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide,carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon,chlorimuron (-ethyl), chlornitrofen, chlorsulphuron, chlortoluron,cinidon (-ethyl), cinmethylin, cinosulphuron, clefoxydim, clethodim,clodinafop (-propargyl), clomazone, clomeprop, clopyralid,clopyrasulphuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl),2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P),diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulphuron (-methyl), ethofumesate, ethoxyfen,ethoxysulphuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide,flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulphuron,florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium),flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin,flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulphuron (-methyl, -sodium),flurenol (-butyl), fluridone, fluoroxypyr (-butoxypropyl, -meptyl),flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen,foramsulphuron, glufosinate (-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl),hexazinone, HOK-201, imazamethabenz (-methyl), imazamethapyr, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulphuron,iodosulphuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon,isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen,lenacil, linuron, MCPA, mecoprop, mefenacet, mesosulphurone, mesotrione,metamifop, metamitron, metazachlor, methabenzthiazuron, metobenzuron,metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin,metsulphuron (-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulphuron, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulphuron,oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin,pendralin, penoxsulam, pentoxazone, phenmedipham, picolinafen,pinoxaden, piperophos, pretilachlor, primisulphuron (-methyl),profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulphuron, pyraflufen (-ethyl), pyrasulfotole, pyrazogyl, pyrazolate,pyrazosulphuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridate, pyridatol, pyriftalide, pyriminobac (-methyl), pyrimisulfan,pyrithiobac (-sodium), pyroxasulfone, quinchlorac, quinmerac,quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulphuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulphuron, tebutam, tebuthiuron, tembotrione,tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide,thiazopyr, thidiazimin, thifensulphuron (-methyl), thiobencarb,tiocarbazil, topramezone, tralkoxydim, triallate, triasulphuron,tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulphuron, triflusulphuron (-methyl), tritosulphuron and

A mixture with other known active compounds, such as fungicides,insectides, acaricides, nematicides, bird repellents, plant nutrientsand soil conditioners, is also possible.

The active compounds or active compound combinations can be applied assuch, in the form of their formulations or the use forms preparedtherefrom by further dilution, such as ready-to-use solutions,suspensions, emulsions, powders, pastes and granules. They are appliedin the customary manner, for example by watering, spraying, atomizing,spreading.

The active compounds or active compound combinations according to theinvention can be applied both before and after plant emergence. They canalso be incorporated into the soil prior to planting.

The application rate of active compound can vary within a substantialrange. Essentially, it depends on the nature of the desired effect. Ingeneral, the application rates are between 1 g and 10 kg of activecompound per hectare of soil area, preferably between 5 g and 5 kg perha.

The advantageous effect of the compatibility with crop plants of theactive compound combinations according to the invention is particularlypronounced at certain concentration ratios. However, the weight ratiosof the active compounds in the active compound combinations can bevaried within relatively wide ranges. In general, from 0.001 to 1000parts by weight, preferably from 0.01 to 100 parts by weight,particularly preferably 0.05 to 20 parts by weight, of one of thecompounds which improves crop plant compatibility (antidotes/safeners)mentioned above under (b′) are present per part by weight of activecompound of the formula (I).

The active compound combinations according to the invention aregenerally applied in the form of finished formulations. However, theactive compounds contained in the active compound combinations can, asindividual formulations, also be mixed during use, i.e. be applied inthe form of tank mixes.

For certain applications, in particular by the post-emergence method, itmay furthermore be advantageous to include, as further additives in theformulations, mineral or vegetable oils which are tolerated by plants(for example the commercial preparation “Rako Binol”), or ammoniumsalts, such as, for example, ammonium sulphate or ammonium thiocyanate.

The novel active compound combinations can be used as such, in the formof their formulations or the use forms prepared therefrom by furtherdilution, such as ready-to-use solutions, suspensions, emulsions,powders, pastes and granules. Application is in the customary mariner,for example by watering, spraying, atomizing, dusting or scattering.

The application rates of the active compound combinations according tothe invention can be varied within a certain range; they depend, interalia, on the weather and on soil factors. In general, the applicationrates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2kg per ha, particularly preferably between 0.01 and 0.5 kg per ha.

The active compound combinations according to the invention can beapplied before and after emergence of the plants, that is to say by thepre-emergence and post-emergence method.

Depending on their properties, the safeners to be used according to theinvention can be used for pretreating the seed of the crop plant (seeddressing) or can be introduced into the seed furrows prior to sowing orbe used separately prior to the herbicide or together with theherbicide, before or after emergence of the plants.

Examples of plants which may be mentioned are important crop plants,such as cereals (wheat, barley, rice), maize, soya beans, potatoes,cotton, oilseed rape, beet, sugar cane and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), particular emphasisbeing given to cereals, maize, soya beans, potatoes, cotton and oilseedrape.

The term “active compounds” always also includes the active compoundcombinations mentioned here.

Preparation and use of the active compounds according to the inventionis illustrated by the examples below.

USE EXAMPLES Example I-a-1

Under argon, 4.26 g of potassium tertbutoxide (36 mmol) are initiallycharged in 10 ml of dimethylacetamide. At −20 to −30° C., 8.5 g (16.4mmol) of the compound according to Example II-1 in 15 ml ofdimethylacetamide are added dropwise. The mixture is stirred at 20° C.for 1 hour (the reaction is monitored by thin-layer chromatography).After the reaction has ended, the reaction solution is stirred into 100ml of ice-water, the pH is adjusted to 2 using concentrated hydrochloricacid and the precipitate is filtered off with suction. The precipitateis redissolved in 40 ml of dichloromethane, and 20 ml of a 0.5 Nsolution of NaOH are added dropwise. The mixture is stirred at 20° C.for 1 hour. The aqueous phase is adjusted to pH 2 and the precipitate isfiltered off with suction.

The product is purified by column chromatography on silica gel(dichloromethane:ethyl acetate=5:3).

Yield: 4.2 g (51% of theory), m.p. 259° C.

Analogously to Example (I-a-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-a) are obtained:

(I-a)

Ex. m. p. No. J X Y D A B °C. Isomer I-a-2 2-OCF₃ H H H—(CH₂)₂—CHOCH₃—(CH₂)₂— 228 β I-a-3 5-OCF₃ 2-Br H H—(CH₂)₂—CHOCH₃—(CH₂)₂— 258 β I-a-4 5-OCF₃ 2-Br H H —(CH₂)₂—O—(CH₂)₂— 138— I-a-5 5-OCF₃ 2-Br H H

230 — I-a-6 5-OCF₃ 2-Br H H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— 96 β I-a-7 4-OCF₃2-Br 6-Br H —CH₂—CHOCH₃—(CH₂)₃— 372 α I-a-8 4-OCF₃ 2-Br 6-CH₃ H—(CH₂)₂—O—(CH₂)₂— *1.46-l.57 (m, 2H, CH₂); 2.20 (s, 3H, Ar—CH₃);3.73-3.79 (m, 2H, OCH₂); 3.99-4.03 (m, 2H, OCH₂); 7.42-7.43 (d, 1H, ArH)I-a-9 4-OCF₃ 2-Br 6-Br H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— 170 β I-a-10 4-OCF₃2-Br 6-Cl H CH₃ CH₃ 108-111 — I-a-11 4-OCF₃ 2-Br 6-Cl H—CH₂—CHOC₄H₉—(CH₂)₃— 110-112 β I-a-12 4-OCF₃ 2-Br 6-Cl —(CH₂)₃— H220-221 — I-a-13 4-OCF₃ 2-Br 6-Cl

CH₃ H 100-102 — I-a-14 4-OCF₃ 2-Br 6-Br H —CH₂—CHOC₄H₉—(CH₂)₃— 106-110 βI-a-15 4-OCF₃ 2-Br 6-Br —(CH₂)₃— H 229-231 — I-a-16 4-OCF₃ 2-Br 6-Br

CH₃ H 108-112 — I-a-17 4-OCF₃ 2-Br 6-Br H

CH₃ 98-100 — I-a-18 4-OCF₃ 2-Br 6-Br H C₂H₅ CH₃ 85-87 — I-a-19 4-OCF₃2-Br 6-Cl H

CH₃ 221-225 — I-a-20 4-OCF₃ 2-Br 6-Cl H C₂H₅ CH₃ 209-212 — I-a-21 4-OCF₃2-OCH₃ 6-Br H CH₃ CH₃ — I-a-22 4-OCF₃ 2-OCH₃ 6-Br H—(CH₂)₂—CHOCH₃—(CH₂)₂— 104-106 β I-a-23 4-OCF₃ 2-OCH₃ 6-Cl H CH₃ CH₃133-136 — I-a-24 4-OCF₃ 2-OCH₃ 6-Cl H —CH₂—CHOC₄H₉—(CH₂)₃— 93-96 βI-a-25 4-OCF₃ 2-OCH₃ 6-Cl —(CH₂)₃— H 170-172 — I-a-26 4-OCF₃ 2-OCH₃ 6-ClH —(CH₂)₂—CHOCH₃—(CH₂)₂— 170-173 β I-a-27 4-OCF₃ 2-OCH₃ 6-Cl H

CH₃ 79-82 — I-a-28 4-OCF₃ 2-OCH₃ 6-Cl H —(CH₂)₂—O—(CH₂)₂— 121 — I-a-294-OCF₃ 2-Cl 6-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— 282 β I-a-30 4-OCF₃ 2-Cl 6-ClH —(CH₂)₂—O—(CH₂)₂— 251 — I-a-31 4-OCF₃ 2-Br 6-Br H CH₃ CH₃ 216 — I-a-324-OCF₃ 2-Br 6-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— 280 β I-a-33 4-OCF₃ 2-Br 6-BrH —CH₂—CHOCH₃—(CH₂)₃— wax β I-a-34 5-OCF₃ 2-Br H H

125 β I-a-35 5-OCF₃ 2-Br H H

189 β I-a-36 4-OCF₃ 2-OCH₃ 6-OCH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— ***3.32 β (m,1H, CHOCH₃); 6.40 (s, 2H, ArH) I-a-37 4-OCF₃ 2-CH₃ 6-CH₃ H—CH₂—CHOC₂H₅—(CH₂)₃— 109-112 β I-a-38 4-OCF₃ 2-CH₃ 6-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 263-265 β I-a-39 4-OCF₃ 2-Cl 6-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 270 β I-a-40 4-OCF₃ 2-Cl 6-CH₃ H—CH₂—CHOCH₃—(CH₂)₂— 202-206 cis I-a-41 4-OCF₃ 2-Cl 6-CH₃ H—CH₂—CHOCH₃—(CH₂)₂— 75-95 trans I-a-42 4-OCF₃ 2-OCH₃ 6-Cl H

decomposition — I-a-43 4-OCF₃ 2-Cl 6-Cl H

272 — I-a-44 4-OCF₃ 2-Br 6-Br H

240 β I-a-45 4-OCF₃ 2-Br 6-Br H

291 — I-a-46 2-OCF₃ 4-Br H H —(CH₂)₂—CHOCH₃—(CH₂)₂— 253 β I-a-47 2-OCF₃4-Cl H H —(CH₂)₂—O—(CH₂)₂— 245 — I-a-48 2-OCF₃ 6-Cl 4-Br H—(CH₂)₂—O—(CH₂)₂— 258 — I-a-49 2-OCF₃ 6-CH₃ 4-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 216-219 β I-a-50 2-OCF₃ 6-CH₃ 4-CH₃ H—CH₂—CHOCH₃—(CH₂)₂— 189-192 β I-a-51 2-OCF₃ 6-OCH₃ 4-Br H—(CH₂)₂—O—(CH₂)₂— 208 — I-a-52 2-OCF₃ 4-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂—239 β I-a-53 2-OCF₃ 6-Br 4-Cl H —(CH₂)₂—O—(CH₂)₂— 275 — I-a-54 2-OCF₃6-OCH₃ 4-Cl H —(CH₂)₂—O—(CH₂)₂— 224 — I-a-55 2-OCF₃ 6-Cl 4-CH₃ H—(CH₂)₂—O—(CH₂)₂— **1.2-1.34 — (m, 2H, CH₂) - 2.37 (s, 3H-ArCH₃3.83-3.88 (m, 2H, OCH₂), 7.14, 7.34 (2s, 2H, ArH) I-a-56 2-OCF₃ 4-Br H H—(CH₂)₂—O—(CH₂)₂— 246 — I-a-57 2-OCF₃ 6-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂—254 β I-a-58 2-OCF₃ 6-Br 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— 280 β I-a-592-OCF₃ 6-Br 4-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— 280 β I-a-60 2-OCF₃ 6-Cl 4-BrH —CH₂—CHOC₂H₅—(CH₂)₃— 73 β I-a-61 2-OCF₃ 6-OCH₃ 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 196-198 β I-a-62 2-OCF₃ 6-Cl 4-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— 209-210 β I-a-63 2-OCF₃ 6-Cl 4-CH₃ H—CH₂—CHOC₂H₅—(CH₂)₃— 189-192 β I-a-64 2-OCF₃ 6-Cl 4-CH₃ H—CH₂—CHOC₃H7—(CH₂)₃— 105-108 β I-a-65 2-OCF₃ 6-OCH₃ 4-Cl H—CH₂—CHOC₂H₅—(CH₂)₃— 89-91 β I-a-66 2-OCF₃ 6-C₂H₅ 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— 237-240 β I-a-67 2-OCF₃ 6-C₂H₅ 4-Cl H

201-204 β I-a-68 2-OCF₃ 6-CH₃ 4-Cl H —CH₂—CHOC₂H₅—(CH₂)₃— 222-223 βI-a-69 2-OCF₃ 6-CH₃ 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— 280-282 β I-a-702-OCF₃ 6-Cl 4-Br H

209 — I-a-71 2-OCF₃ 6-Cl 4-Br H CH₃ CH₃ 181 — I-a-72 2-OCF₃ 6-Cl 4-Br H

257 — I-a-73 2-OCF₃ 6-C₂H₅ 4-Cl —(CH₂)₃— H 217-220 *¹H-NMR (400 MHz,d₄-methanol): shifts δ in ppm **¹H-NMR (400 MHz, d₆-DMSO): shifts δ inppm ***¹H-NMR (400 MHz, CDCl₃): shifts δ in ppm

Example I-b-1

Under argon, 0.5 g (1 mmol) of the compound according to Ex. I-a-1 areinitially charged in ethyl acetate, 0.14 ml of triethylamine plus 10 mgof Steglich base are added and 0.1 ml of 2-methyl-propionyl chloridedissolved in 5 ml of ethyl acetate are added dropwise at reflux, and themixture is then stirred under reflux.

After the reaction has ended (the reaction is monitored by thin-layerchromatography), the mixture is separated by RP column chromatography(water/acetonitrile:50/50→10/90).

Yield: 0.23 g (40% of theory), m.p. 219° C.

Analogously to Example (I-b-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-b) are obtained:

(I-b)

Ex. m.p. No. J X Y D A B R¹ ° C. Isomer I-b-2 5-OCF₃ 2-Br H H—(CH₂)₂—CHOCH₃—(CH₂)₂— i- 165 β C₃H₇ I-b-3 5-OCF₃ 2-Br H H

i- C₃H₇ 156 β I-b-4 4-OCF₃ 2-Br 6-Cl

CH₃ H i- C₃H₇ oil, * 1) — I-b-5 4-OCF₃ 2-Br 6-Br H —CH₂—CHOC₄H₉—(CH₂)₃—i- 182- β C₃H₇ 185 I-b-6 4-OCF₃ 2-Br 6-Cl H

CH₃ i- C₃H₇ 156- 159 — I-b-7 4-OCF₃ 2-Br 6-Br H

CH₃ i- C₃H₇ 150- 156 — I-b-8 4-OCF₃ 2-Br 6-Br H C₂H₅ CH₃ i- 129- — C₃H₇132 I-b-9 4-OCF₃ 2-Br 6-Cl H —CH₂—CHOC₄H₉—(CH₂)₃— i- 183- β C₃H₇ 186I-b-10 4-OCF₃ 2-Br 6-Br —(CH₂)₃— H i- ** 2) — C₃H₇ I-b-11 4-OCF₃ 2-Br6-Cl

CH₃ H i- C₃H₇ ** 3) — I-b-12 4-OCF₃ 2-Br 6-Cl H C₂H₅ CH₃ i- 135- — C₃H₇141 I-b-13 4-OCF₃ 2- 6-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— i- 204 β OCH₃ C₃H₇I-b-14 4-OCF₃ 2-Br 6-Cl —(CH₂)₃— H i- ** 4) — C₃H₇ I-b-15 4-OCF₃ 2- 6-ClH —CH₂—CHOC₄H₉—(CH₂)₃— i- 178- β OCH₃ C₃H₇ 186 I-b-16 4-OCF₃ 2- 6-Cl—(CH₂)₃— H i- ** 5) — OCH₃ C₃H₇ I-b-17 4-OCF₃ 2- 6-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— i- 198 β OCH₃ C₃H₇ I-b-18 4-OCF₃ 2- OCH₃ 6-Cl H

CH₃ i- C₃H₇ 153- 174 — I-b-19 4-OCF₃ 2- 6-Cl H CH₃ CH₃ i- 110- — OCH₃C₃H₇ 118 I-b-20 4-OCF₃ 2-Cl 6-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— i- 190 β C₃H₇I-b-21 4-OCF₃ 2-Cl 6- H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 212 β CH₃ I-b-224-OCF₃ 2-Cl 6- H —(CH₂)₂—CHOCH₃—(CH₂)₂— i- 159- β CH₃ C₃H₇ 161 I-b-234-OCF₃ 2-Br 6-Br H

i- C₃H₇ 204 β I-b-24 2-OCF₃ 6-CH₃ 4- H —CH₂—CHOC₂H₅—(CH₂)₃— CH₃ 228- βCH₃ 230 I-b-25 2-OCF₃ 6-CH₃ 4- H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 202- β CH₃205 I-b-26 2-OCF₃ 6-CH₃ 4- H —(CH₂)₂—CHOCH₃—(CH₂)₂— i- 207 β CH₃ C₃H₇I-b-27 2-OCF₃ 6-C₂H₅ 4-Cl H

i- C₃H₇ * 6) β I-b-28 2-OCF₃ 6-CH₃ 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ *7) β 1) 2.61 (m, 1H, CH (C5)); 2.70 (m, 1H (CH (CH₃)₂); 7.31, 7.44 (ineach case dd, 1H, ArH) 2) 2.70 (m, 1H, CH (CH₃)₂); 4.79 (m, 1H, CH(C5);7.47 (dd, 2-H, ArH) 3) 2.62 (m, 1H, CH(C5); 2.70 (m, 1H, CH(CH₃)₂; 7.47(dd, 1H ArH) 4) 2.67 (m, 1H, CH( CH₃)₂; 4.75 (m, 1H, CH(C5); 7.31, 7.43(in each case dd, 1H, ArH) 5) 2.66 (m, 1H, CH (CH₃)₂; 4.70 (m, 1H,CH(C5); 6.68, 6.96 (in each case dd, 1H, ArH) 6) 2.62 (m, 1H, CH(CH₃)₂);2.71 (m, 2H, Ar CH₂(CH₃); 3.36 (s, 3H, OCH₃) 7) 2.1 (s, 3H, COCH₃); 2.33(s, 3H, ArCH₃); 3.40 (s, 3H, OCH₃) *¹H-NMR (400 MHz, CDCl₃): shift δ inppm **¹H-NMR (300 MHz, CDCl₃): shift δ in ppm

Example I-c-1

Under argon, 0.5 g (1 mmol) of the compound according to Ex. I-a-1 isinitially charged in methylene chloride, 0.14 ml of triethylamine isadded, at about 20° C. the chloroformic ester (0.1 ml), dissolved in 5ml of dichloromethane, is added dropwise and the mixture is stirred atfrom 20 to 30° C.

After the reaction has ended (the reaction is monitored by thin-layerchromatography), the mixture is separated by RP column chromatography(water/acetonitrile:50/50→10/90).

Yield: 0.415 g (74% of theory), m.p. 194° C.

Analogously to Example (I-c-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-c) are obtained:

(I-c)

Ex. No. J X Y D A B M R² m.p. ° C. Isomer I-c-2 5-OCF₃ 2-Br H H—(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 161 β I-c-3 5-OCF₃ 2-Br H H

O C₂H₅ 201 — I-c-4 5-OCF₃ 2-Br H H

O C₂H₅ 182 β I-c-5 4-OCF₃ 2-Br 6-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 166β I-c-6 4-OCF₃ 2-Br 6-Cl H —CH₂—CHOC₄H₉—(CH₂)₃— O C₂H₅ 184 β I-c-74-OCF₃ 2-Br 6-Cl —(CH₂)₃— H O C₂H₅ * 1) — I-c-8 4-OCF₃ 2-Br 6-Cl

CH₃ H O C₂H₅ viscous oil * 2) — I-c-9 4-OCF₃ 2-Br 6-Br H—CH₂—CHOC₄H₉—(CH₂)₃— O C₂H₅ 201 β I-c-10 4-OCF₃ 2-Br 6-Br —(CH₂)₃— H OC₂H₅ viscous — oil * 3) I-c-11 4-OCF₃ 2-Br 6-Br

CH₃ H O C₂H₅ viscous oil * 4) — I-c-12 4-OCF₃ 2-Br 6-Cl H

CH₃ O C₂H₅ 143 — I-c-13 4-OCF₃ 2-Br 6-Br H

CH₃ O C₂H₅ 126- 130 — I-c-14 4-OCF₃ 2-Br 6-Br H C₂H₅ CH₃ O C₂H₅ 110- —114 I-c-15 4-OCF₃ 2-Br 6-Cl H C₂H₅ CH₃ O C₂H₅ 130- — 131 I-c-16 4-OCF₃2- 6-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 177- β OCH₃ 179 I-c-17 4-OCF₃ 2-6-Cl H —CH₂—CHOC₄H₉—(CH₂)₃— O C₂H₅ 188- β OCH₃ 190 I-c-18 4-OCF₃ 2- 6-ClH —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 147- β OCH₃ 150 I-c-19 4-OCF₃ 2- 6-Cl—(CH₂)₃— H O C₂H₅ *1.30 — OCH₃ (m, 3H, O—CH, CH₃), 4.67 (m, 1H,

6.52, 6.92 (2d, in each case 1H, Ar—H) I-c-20 4-OCF₃ 2-Cl 6-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 164 β I-c-21 4-OCF₃ 2-Cl 6-Cl H—(CH₂)₂—O—(CH₂)₂— O C₂H₅ 212 — I-c-22 4-OCF₃ 2-CH₃ 6-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 182- β 183 I-c-23 4-OCF₃ 2-CH₃ 6-CH₃ H—CH₂—CHOC₂H₅—(CH₂)₃— O C₂H₅ 205- β 206 I-c-24 4-OCF₃ 2-Cl 6-CH₃ H—CH₂—CHOCH₃—(CH₂)₂— O C₂H₅ 86-89 cis I-c-25 4-OCF₃ 2-Cl 6-CH₃ H—CH₂—CHOCH₃—(CH₂)₂— O C₂H₅ 146- trans 149 I-c-26 4-OCF₃ 2-Cl 6-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 163- β 165 I-c-27 4-OCF₃ 2-Br 6-Br H

O C₂H₅ 201 β I-c-28 2-OCF₃ 6- 4-Cl —(CH₂)₃— H O CH₂—C₆H₅ * 5) — C₂H₅I-c-29 2-OCF₃ 6-CH₃ 4-CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 210- β 212I-c-30 2-OCF₃ 6-CH₃ 4-CH₃ H —CH₂—CHOC₂H₅—(CH₂)₃— O C₂H₅ 203 β I-c-312-OCF₃ 6- 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 168- β OCH₃ 170 I-c-322-OCF₃ 6- 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 139- β C₂H₅ 141 I-c-332-OCF₃ 6- C₂H₅ 4-Cl H

O C₂H₅ 160- 162 β I-c-34 2-OCF₃ 6-CH₃ 4-Cl H —CH₂—CHOC₂H₅—(CH₂)₃— O C₂H₅186- β 188 I-c-35 2-OCF₃ 6- 4-Cl H —CH₂—CHOC₂H₅—(CH₂)₃— O C₂H₅ 186- βOCH₃ 187 I-c-36 2-OCF₃ 6-Cl 4-CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ 227- β228 I-c-37 2-OCF₃ 6-Cl 4-CH₃ H —CH₂—CHOC₂H₅—(CH₂)₃— O C₂H₅ 144- β 145I-c-38 2-OCF₃ 6-CH₃ 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— O C₂H₅ * 6 β I-c-392-OCF₃ 6- 4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— O CH₃ * 7 β C₂H₅ 1) 4.29 (m, 2H,OCH₂—CH₃); 4.81 (m, 1H, CH (C5)); 7.33, 7.47 (in each case dd, 1H, ArH)2) 2.62 (m, 1H, CH (C5)); 4.26 (m, 2H, OCH₂CH₃); 7.32, 7.45 (in eachcase dd, 1H, ArH) 3) 4.27 (q, 2H, OCH₂); 4.80 (m, 1H, CH (C5);7.47 (dd,2H, ArH) 4) 2.62 (m, 1H, CH (C5); 4.26 (m, 2H, OCH₂); 7.47 (d, 2H, ArH)5) 1.08 (m, 3H, Ar—CH₂—CH₃); 4.76 (m, 1H, CH (C5); 5.2 (d, 2H, O—CH₂) 6)2.33 (s, 3H, Ar CH₃); 3.38 (s, 3H, OCH₃); 4.08 (q, 2 H, OCH₂) 7) 2.67(m, 2H, Ar—CH₂—CH₃); 3.37 (s, 3H, OCH₃); 3.69 (s, 3H CO₂CH₃) *¹H-NMR(400 MHz, CDCl₃): shift δ in ppm **¹H-NMR (300 MHz, CDCl₃): shift δ inppm:

Example I-d-1

0.15 g (0.41 mmol) of the compound according to Example (I-a-73), 0.05 gof triethylamine and mg of 4-N,N′-dimethylaminopyridine are initiallycharged in 5 ml of chloroform. After 10 min of stirring, 0.05 g (0.45mmol) of methanesulphonyl chloride are added, and the mixture is stirredfurther at room temperature overnight. The mixture is added to 5 ml of5% strength sodium bicarbonate solution and stirred at room temperaturefor 10 min, and the organic phase is separated off, dried over sodiumsulphate and concentrated using a rotary evaporator. This is followed bychromatographic purification on silica gel on a Biotage separating unitusing a gradient (ethyl acetate:n-heptane 1:4 to 4:1). Yield: 0.052 g(28% of theory)

¹H-NMR (300 MHz, CDCl₃): δ=3.04 (s, 3H, SOCH ₃), 4.64 (m, 1H, CH(C5),7.16, 7.22 (in each case dd, 1H, Ar—H) ppm.

Example I-f-1

0.15 g (0.38 mmol) of the compound according to Example (I-a-50) areinitially charged in 6 ml of methanol, and 0.07 ml of a 30% strengthsodium methoxide solution is added. After 2 h of stirring at roomtemperature, the mixture is concentrated and the residue is dried underhigh vacuum. This gives 0.155 g (=97% of theory) of a solid.

¹H-NMR (400 MHz, D₂O): δ=3.67 (m, 3H, O—CH and O—CH ₂), 7.05, 7.13 (ineach case d, 1H, ArH) ppm.

Analogously to Example (I-f-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-f) are obtained:

(I-f)

Ex.- Iso- No. J X Y D A B E NMR mer I-f-2 2-OCF₃ 6-C₂H₅ 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— Na⁺ *1) β I-f-3 2-OCF₃ 4-CH₃ 6-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— Na⁺ *2) β 1) 3.23 (s, 3H, OCH₃); 6.98, 7.11 (ineach case d, 1H, ArH) 2) 3.16 (s, 3H, OCH₃); 6.72, 7.85 (in each case d,1H, Ar—H) *¹H-NMR (400 MHz, d₆-DMSO): shift δ in ppm

Example II-1

Under argon, 4.3 g (22 mmol) of methyl1-aminotetrahydropyranylcarboxylate×HCl are initially charged in 40 mlof anhydrous tetrahydrofuran, and 6.2 ml (44 mmol) of triethylamine areadded. The mixture is stirred for 5 min, and 7.6 g of2,6-dibromo-4-trifluoromethoxyphenylacetic acid are added, the mixtureis stirred at room temperature for another 15 min, 4.4 ml oftriethylamine are added and 1.2 ml of phosphorus oxychloride areimmediately added dropwise such that the solution is boiling gently. Themixture is stirred under reflux for 30 min. The reaction mixture isconcentrated under reduced pressure and the residue is purified bycolumn chromatography on silica gel (dichloromethane/ethyl acetate=3:1).

Yield: 8.5 g (79% of theory), m.p.: 212° C.

Example II-19

3.46 g (8.13 mmol) of the compound according to Example XIX-1 in 10 mlof dichloromethane are added to 2.513 ml of sulphuric acid. The mixtureis stirred at 35° C. for 3 h, and 20 ml of methanol are added. Themixture is stirred at 60° for 4 h and then stirred at room temperatureovernight. A further 2 ml of sulphuric acid are added, since there isstill some starting material left. The mixture is stirred at 60° C. for4 h. The mixture is checked for conversion by thin-layer chromatography,the reaction solution is then added to 100 ml of water and the organicphase is separated off and dried over sodium sulphate. The solvent isthen removed on a rotary evaporator.

Yield: 3.31 g (88% of theory)

Analogously to Examples (II-1) and (II-19) and according to the generalstatements on the preparation, the following compounds of the formula(II) are obtained:

(II)

Ex. No. J X Y D A B R⁸ m.p. ° C. Isomer II-2 2-OCF₃ H H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 105 β II-3 5-OCF₃ 2-Br H H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ oil β II-4 5-OCF₃ 2-Br H H —(CH₂)₂—O—(CH₂)₂—CH₃ 125 — II-5 5-OCF₃ 2-Br H H

CH₃ 138 — II-6 5-OCF₃ 2-Br H H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— CH₃ 100 β II-74-OCF₃ 2-Br 6-Br H —CH₂—CHOCH₃—(CH₂)₃— CH₃ 102 β II-8 5-OCF₃ 2-Br H H

CH₃ Wax β II-9 4-OCF₃ 2-Br 6-Br H —(CH₂)₂—CHOC₂H₅—(CH₂)₂— CH₃ 186 βII-10 4-OCF₃ 2-Br 6-Cl H CH₃ CH₃ CH₃ 127-129 — II-11 4-OCF₃ 2-Br 6-Cl H—CH₂—CHOC₄H₉—(CH₂)₃— CH₃ *0.89 (t, 3H, CH₃) trans 3.97 (d, 2H, Ar—CH₂),7.32 and 7.44 (in each case s, 1H, Ar—H) II-12 4-OCF₃ 2-Br 6-Cl —(CH₂)₃—H CH₃ *4.02 (d, 2H, Ar—CH₂) — 7.26 and 7.38 (in each case s, 1H, Ar—H),4.53 (m, 1H, C(2)-H) II-13 4-OCF₃ 2-Br 6-Cl

CH₃ H CH₃ *1.51 (d, 3H, CH₃) 4.24 (s, 2H, Ar—CH₂) 7.26 and 7.38 (in eachcase s, 1H, Ar—H) — II-14 4-OCF₃ 2-Br 6-Br H —CH₂—CHOC₄H₉—(CH₂)₃— CH₃*0.91 (t, 3H, CH₃) β 4.03 (s, 2H, Ar—CH₂) 7.51 (s, 2H, Ar—H) II-154-OCF3 2-Br 6-Br —(CH₂)₃— H CH₃ *4.53 (m, 1H, C(2)- — H, 4.09 (d, 2H,Ar—CH₂) 7.44 (s, 2H, Ar—H) II-16 4-OCF₃ 2-Br 6-Br

CH₃ H CH₃ *1.51 (d, 3H, CH₃) 4.31 (s, 2H, Ar—CH₂) 7.44 (s, 2H, Ar—H) —II-17 4-OCF₃ 2-Br 6-Br H

CH₃ CH₃ **1.29 (m, 1H, CH-cyclopropyl), 3.98 (d, 2H, Ar—CH₂) 7.47 (s,2H, Ar—H) — II-18 4-OCF₃ 2-Br 6-Br H C₂H₅ CH₃ CH₃ **1.60 (s, 3H, CH₃—) —4.01 (d, 2H, Ar—CH₂) 7.47 (s, 2H, Ar—H) II-19 4-OCF₃ 2-Br 6-Cl H

CH₃ CH₃ **1.46 (s, 3H, CH₃)—, 3.94 (d, 2H, Ar—CH₂) 7.30 and 7.43 (ineach case s, 1H, Ar—H) — II-20 4-OCF₃ 2-Br 6-Cl H C₂H₅ CH₃ CH₃ **1.59(s, 3H, CH₃) — 3.97 (d, 2H, Ar—CH₂) 7.30 and 7.43 (in each case s, 1H,Ar—H) II-21 4-OCF₃ 2-OCH₃ 6-Br H CH₃ CH₃ CH₃ 110° C. — II-22 4-OCF₃2-OCH₃ 6-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ **3.33 (s, 3H, CH—OCH₃) β OCH₃)6.72 and 7.11 (in each case s, 1H, Ar—H) II-23 5-OCF₃ 2-Br H H

CH₃ 117 β II-24 4-OCF₃ 2-OCH₃ 6-Cl H —CH₂—CHOC₄H₉—(CH₂)₃— CH₃ **0.93 (t,3H, CH₃) β 3.91 (d, 2H, Ar—CH₂) 6.71 and 6.98 (in each case s, 1H, Ar—H)II-25 4-OCF₃ 2-OCH₃ 6-Cl —(CH₂)₃— H CH₃ **3.68 (s, 3H, — Ar—OCH₃) 4.53(m, 1H, C(2)- H) 6.63 and 6.91 (in each case s, 1H, Ar—H) II-26 4-OCF₃2-OCH₃ 6-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ **3.33 (s, 3H, CH—OCH₃) β 6.84and 6.96 (s, 1H, Ar—H) II-27 4-OCF₃ 2-OCH₃ 6-Cl H —(CH₂)₂—O—(CH₂)₂— CH₃170 — II-28 4-OCF₃ 2-Cl 6-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 168 β II-294-OCF₃ 2-Cl 6-Cl H —(CH₂)₂—O—(CH₂)₂— CH₃ 182 — II-30 4-OCF₃ 2-Br 6-Br HCH₃ CH₃ CH₃ 170 — II-31 4-OCF₃ 2-Br 6-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃180 β II-32 4-OCF₃ 2-Br 6-Br H —CH₂—CHOCH₃—(CH₂)₃— CH₃ oil α II-344-OCF₃ 2-OCH₃ 6-OCH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 137-139 β II-35 4-OCF₃2-CH₃ 6-CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 164-168 β II-36 4-OCF₃ 2-CH₃6-CH₃ H —CH₂—CHOC₂H₅—(CH₂)₃— CH₃ 141-144 β II-37 4-OCF₃ 2-Cl 6-CH₃ H—CH₂—CHOCH₃—(CH₂)₂— C₂H₅ ** 1) mixture about 1:1 II-38 4-OCF₃ 2-Cl 6-CH₃H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 164 β II-39 4-OCF₃ 2-Br 6-Br H

CH₃ 180 — II-40 4-OCF₃ 2-OCH₃ 6-Cl H

CH₃ 143 — II-41 4-OCF₃ 2-Cl 6-Cl H

CH₃ 160 — II-42 4-OCF₃ 2-Br 6-Br H

CH₃ 173 β II-43 2-OCF₃ 4-Br H H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 134 β II-442-OCF₃ 4-Cl H H —(CH₂)₂—O—(CH₂)₂— CH₃ 132 — II-45 2-OCF₃ 6-Cl 4-Br H—(CH₂)₂—O—(CH₂)₂— CH₃ 144 — II-46 2-OCF₃ 4-Cl H H —(CH₂)₂—CHOCH₃—(CH₂)₂—CH₃ 133 β II-47 2-OCF₃ 6-CH₃ 4-CH₃ H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 138 βII-48 2-OCF₃ 6-CH₃ 4-CH₃ H —CH₂—(CHOC₂H₅—(CH₂)₃— CH₃ ** 2) β II-492-OCF₃ 4-Br H H —(CH₂)₂O—(CH₂)₂— CH₃ 142 — II-50 2-OCF₃ 6-OCH₃ 4-Br H—(CH₂)₂—O—(CH₂)₂— CH₃ 182 — II-51 2-OCF₃ 6-Br 4-Cl H —(CH₂)₂—O—(CH₂)₂—CH₃ 160 — II-52 2-OCF₃ 6-OCH₃ 4-Cl H —(CH₂)₂—O—(CH₂)₂— CH₃ 181 — II-532-OCF₃ 6-Cl 4-Br H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 131 β II-54 2-OCF₃ 6-Cl4-Br H —CH₂—CHOC₂H₅—(CH₂)₃— CH₃ 128 β II-55 2-OCF₃ 6-Br 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 144 β II-56 2-OCF₃ 6-Br 4-Br H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 138 β II-57 2-OCF₃ 6-Cl 4-Br H

CH₃ 155 — II-58 2-OCF₃ 6-Cl 4-Br H CH₃ CH₃ CH₃ 129 — II-59 2-OCF₃ 6-OCH₃4-Cl H —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ ** 3 β II-60 2-OCF₃ 6-Cl 4-CH₃ H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 150-151 β II-61 2-OCF₃ 6-Cl 4-CH₃ H—CH₂—CHOC₂H₅—(CH₂)₃— CH₃ 120-123 β II-62 2-OCF₃ 6-Cl 4-CH₃ H—CH₂—CHOC₃H₇—(CH₂)₃— CH₃ *** 4 β II-63 2-OCF₃ 6-CH₃ 4-Cl H—CH₂—CHOC₂H₅—(CH₂)₃— CH₃ *** 5 β II-64 2-OCF₃ 6-OCH₃ 4-Cl H—CH₂—CHOC₂H₅—(CH₂)₃— CH₃ ** 6 β II-65 2-OCF₃ 6-C₂H₅ 4-Cl H—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ ** 7 β II-66 2-OCF₃ 6-C₂H₅ 4-Cl H

CH₃ ** 8 β 1) 3.11, 3.29 (in each case s, together 3H, OCH₃); 4.16 (m,2H, OCH₂CH₃) 2) 3.08 (m, 1H, OCH); 3.63(s, 2H, CH₂); 3.68(s, 3H, OCH₃)3) 3.19 (m, 1H, OCH); 3.68(s, 3H, OCH₃); 3.90(s, 3H, Ar OCH₃) 4) 3.21(m,1H, OCH); 3.68(s, 3H, OCH₃); 3.76(s, 2H, CH₂) 5) 3.11 (m, 1H, OCH);3.62(s, 3H, OCH₃); 3.76(s, 2H, CH₂) 6) 3.15 (m, 1H, OCH); 3.60(s, 2H,CH₂); 3.67(s, 3H, OCH₃) 7) 3.15(m, 1H, OCH); 3.63(s, 2H, CH₂); 3.66(s,3H, OCH₃) 8) 3.31(s, 3H, CH₂—OCH₃); 3.63(s, 2H, CH₂); 3.66(s, 3H, OCH₃)*¹H-NMR (500 MHz, CDCl₃): shifts δ in ppm **¹H-NMR (400 MHz, CDCl₃):shifts δ in ppm ***¹H-NMR (300 MHz, CDCl₃): shifts δ in ppm

Example XIX-1

3 g (9 mmol) of the compound according to Ex. XVII-2 are initiallycharged, 1 drop of DMF is added, 3.21 g (27 mmol) of thionyl chlorideare added. The mixture is stirred until the evolution of gas has ceased,the SOCl₂ is removed on a rotary evaporator, the residue is taken up in3 ml of dichloromethane (=solution 1).

2.62 ml of triethylamine are initially charged in 10 ml ofdichloromethane, solution 1 is slowly added dropwise at 0° C. Themixture is stirred overnight at room temperature until all the startingmaterial has been consumed, 10 ml of water are added, the mixture isstirred at room temperature for 10 min and then extracted, the organicphase is dried over sodium sulphate and concentrated using a rotaryevaporator.

The product is reacted further without purification.

Yield: 3.46 g (90% of theory)

1.79 (s 3H, CH₃)

3.98 (s, 2H, Ar—CH₂)

7.32 and 7.44 (in each case s, 1H, Ar—H)

*¹H-NMR (500 MHz, CDCl₃) shift δ in ppm.

Analogously to Example (XIX-1) and according to the general statementson the preparation, the following compounds of the formula (XIX) areobtained:

(XIX)

Ex. No. J X Y A B m.p. ° C. XIX- 4-OCF₃ 2-Br 6-CI C₂H₅ CH₃ *1.67 (s, 3H,CH₃) 2 3.97 (s, 2H, Ar—CH₂) 7.31 and 7.43 (in each case s, 1H, Ar—H)XIX- 3 4-OCF₃ 2-Br 6-Br

CH₃ *1.80 (s, 3H, CH₃) 4.02 (s, 2H, Ar—CH₂) 7.49 (s, 2H, Ar—H) XIX-4-OCF₃ 2-Br 6-Br C₂H₅ CH₃ 130-132 4 where D = H *¹H-NMR (500 MHz, CDCl₃)shift δ in ppm.

Example XVII-1

465 g (1.53 mol) of the compound according to Ex. No. XX-1 are initiallycharged in 10% strength NaOH (1795.87 g=4.49 mmol) at room temperature,and heated to 40° C. The mixture is stirred at 40° C. (the reaction ismonitored by thin-layer chromatography). After the reaction has ended,250 ml of dichloromethane are added, the organic phase is removed, theaqueous phase is acidified with conc. HCl and the precipitate isfiltered off with suction.

Yield: 278 g (59% of theory)

Analogously to Example (XVII-1) and according to the general statementson the preparation, the following compounds of the formula (XVII) areobtained:

(XVII)

Ex. No. J X Y m.p. ° C. XVII-2 4-OCF₃ 2-Br 6-Cl 144-145 XVII-3 4-OCF₃2-Br 6-Br 165-166 XVII-4 4-OCF₃ 2-OCH₃ 6-Br 149-150 XVII-5 4-OCF₃ 2-OCH₃6-CI 135-137 XVII-6 4-OCF₃ 2-Cl 6-Cl 124 XVII-7 4-OCF₃ 2-OCH₃ 6-Cl136-137 XVII-8 4-OCF₃ 2-OCH₃ 6-Br 148-149 XVII-9 4-OCF₃ 2-CH₃ 6-CH₃144-147 XVII-10 4-OCF₃ 2-Cl 6-CH₃ 116-120 XVII-11 2-OCF₃ 2-Cl 4-Br 130XVII-12 2-OCF₃ 6-CH₃ 4-CH₃ 140 XVII-13 2-OCF₃ 6-OCH₃ 4-Cl 138-140XVII-14 2-OCF₃ 6-Cl 4-CH₃ 121-124 XVII-15 2-OCF₃ 6-C₂H₅ 4-Cl 107-108

Example XX-1

423.98 g of potassium hydroxide are initially charged in 2000 ml ofmethanol, the mixture is heated at 50° C., the compound according to Ex.XXI-1 is dissolved in 1474 ml of methanol and added dropwise. Themixture is stirred at about 55° C. overnight and then cooled, the pH isadjusted to 3 using conc. sulphuric acid and the mixture is stirredunder reflux for 1 hour.

The solvent is distilled off and the precipitate is taken up in 500 mlof dichloromethane and 500 ml of water. The organic phase is separatedoff and the solvent is distilled off.

Yield: 465 g (52% of theory)

The compound XX-1 is used further without further purification toprepare compound XVII-1.

Example XX-5

A reaction mixture consisting of 1 g (2.88 mmol) of the compoundaccording to Example (XX-2), 1.56 g (8.6 mmol) of 30% strength sodiummethoxide solution, 0.083 g (0.57 mmol) of copper(I) bromide and 0.78 g(10.5 mmol) of methyl acetate is stirred at a bath temperature of 120°C. for about 7 h. The mixture is taken up in water and filtered, and thefiltrate is adjusted with 1N HCl to pH 1 and extracted with ethylacetate (EA), dried over sodium sulphate and concentrated using a rotaryevaporator. Purification is carried out by column chromatography onsilica gel using EA/n-heptane 1:1

Yield: 0.6 g (=69% of theory)

For spectroscopic data see table with examples of the formula (XX).

Example XX-13

2 g (5.7 mmol) of the compound according to Example (XX-14) areinitially charged in 40 ml of dioxane and 4 ml of water, and 1.11 g (8mmol) of potassium carbonate, 1.98 g (1.7 mmol) oftetrakistriphenylphosphinepalladium and 1.08 g (8.6 mmol) oftrimethylboroxine are added. The reaction mixture is stirred underreflux for 4 hours and then concentrated, taken up in 50 ml of 1N HCland extracted twice with 20 ml of ethyl acetate (EA), and the organicphase is dried over sodium sulphate and concentrated using a rotaryevaporator. The residue is purified on silica gel using EA/n-heptane1:9.

Yield: 1 g (=61% of theory)

For spectroscopic data see table with examples of the formula (XX).

Analogously to Examples (XX-1), (XX-5) and (XX-13), it is possible toprepare the following compounds of the formula (XX):

(XX)

Ex. No. J X Y ¹H-NMR data XX-2 4-OCF₃ 2-Br 6-Cl direct conversion intoXVII-2 XX-3 4-OCF₃ 2-Br 6-Br direct conversion into XVII-3 XX-4 4-OCF₃2-OCH₃ 6-Br *3.71 (s, 3H, OCH₃) 3.81 (s, 3H, CO₂CH₃) 3.84 (s, 2H,Ar—CH₂) 6.68, 7.09 (2s, 2H—Ar—H) XX-5 4-OCF₃ 2-OCH₃ 6-Cl *3.68 (s, 3H,OCH₃) 6.63, 6.91 (2s, 2H, Ar—H) XX-6 4-OCF₃ 2-CH₃ 6-CH₃ m.p. 47° C. XX-74-OCF₃ 2-Br 6-Cl **3.74 (s, 3H, OCH₃) 4.05 (s, 2H, CH₂) 7.28, 7.41 (ineach case s, 1H, ArH) XX-8 4-OCF₃ 2-Cl 6-CH₃ **3.71 (s, 3H, OCH₃) 3.83(s, 2H, CH₂) 6.99, 7.14 (in each case s, 1H, ArH) XX-9 2-OCF₃ 6-Br 4-Br**3.72 (s, 3H, OCH₃) 3.87 (s, 2H, CH₂) 7.41, 7.71 (in each case s, 1H,ArH) XX-10 2-OCF₃ 6-CH₃ 4-CH₃ **3.68 (s, 3H, OCH₃) 3.70 (s, 2H, CH₂)6.92, 6.96 (in each case s, 1H, ArH) XX-11 2-OCF₃ 6-OCH₃ 4-Cl **3.67 (s,2H, CH₂) 3.70 (s, 3H, OCH₃) 3.85 (s, 3H, ArOCH₃) 6.84, 6.95 (in eachcase s, 1H, ArH) XX-12 2-OCF₃ 6-CH₃ 4-Cl ***3.71 (pseudo s, 5H, CH₂ andOCH₃) 7.16 (s, 2H, ArH) XX-13 2-OCF₃ 6-Cl 4-CH₃ ***3.71 (s, 3H, OCH₃)3.84 (s, 2H, CH₂) 7.03, 7.21 (in each case s, 1H, ArH) XX-14 2-OCF₃ 6-Cl4-Br *3.71 (s, 3H, OCH₃) 3.83 (s, 3H, CH₂) 7.37, 7.54 (in each case 2d,1H, ArH) *¹H-NMR (500 MHz, CDCl₃): shifts δ in ppm **¹H-NMR (300 MHz,CDCl₃): shifts δ in ppm ***¹H-NMR (400 MHz, CDCl₃): shifts δ in ppm

Example XXI-1

At room temperature, tert-butyl nitrite (229.9 g=2.23 mol) andcopper(II) chloride (233.9 g=1.74 mol) are initially charged in 1500 mlof acetonitrile. Vinylidene chloride (733.6 g=7.57 mmol) is added over aperiod of 40 min, and 2,6-dichloro-4-trifluoromethoxyaniline (400 g=1.3mmol) in 1350 ml of acetonitrile is then added dropwise over a period of5 h at about 40° C. (slightly exothermic, immediate evolution of gas).After the evolution of gas has ended, the temperature is increased to60° C. and the mixture is stirred for about 18 hours.

The reaction mixture is added to 4 liters of a 1N HCl solution, theorganic phase is separated off, the aqueous phase is extracted with 300ml of methyl tert-butyl ether, the organic phases are washed with 2liters of a 1N HCl solution and the organic phase is separated off. Thesolvent is distilled off.

Yield: 573 g (53% of theory)

Analogously to Example (XXI-1), it is possible to prepare the followingcompounds of the formula (XXI):

(XXI)

Ex. No. J X Y XXI-2 4-OCF₃ 2-Br 6-Cl XXI-3 4-OCF₃ 2-Br 6-Br

Without further purification, the compounds of the formula XXI are usedfor preparing the compounds of the formula XX.

Example No. 1 Myzus Test MYZUPE Spray Treatment

Solvents:

-   -   78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide        Emulsifier:    -   0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of Chinese cabbage (Brassica pekinensis) which are infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After the desired period of time, the effect in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 g/ha, an efficacy of ≧80%:

Ex. No. I-c-5

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an efficacy of ≧80%:

Ex. No. I-a-1, I-a-2, I-a-4, I-a-5, I-a-6, I-a-7, I-a-8, I-a-9, I-a-11,I-a-14, I-a-22, I-a-26, I-a-28, I-a-29, I-a-30, I-a-33, I-a-34, I-a-35,I-a-37, I-a-38, I-a-39, I-a-40, I-a-42, I-a-43, I-a-44, I-a-45, I-a-46,I-a-48, I-a-49, I-a-50, I-a-52, I-a-53, I-a-54, I-a-55, I-a-57, I-a-58,I-a-59, I-a-60, I-a-62, I-a-63, I-a-66, I-a-67, I-a-70, I-b-2, I-b-3,I-b-10, I-b-13, I-b-17, I-b-20, I-b-21, I-b-22, I-b-23, I-b-24, I-b-25,I-b-26, I-c-1, I-c-2, I-c-3, I-c-4, I-c-16, I-c-18, I-c-20, I-c-22,I-c-24, I-c-25, I-c-26, I-c-27, I-c-30, I-c-31, I-c-33, I-c-36

Example No. 2 Tetranychus Test; OP Resistant TETRUR Spray Treatment

Solvents:

-   -   78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide        Emulsifier:    -   0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of bean leaves (Phaseolus vulgaris) which are infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aresprayed with an active compound preparation of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 g/ha, an efficacy of ≧80%:

Ex. No. I-a-38, I-b-22, I-c-26

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 g/ha, an efficacy of ≧80%:

Ex. No. I-a-1, I-a-7, I-a-8, I-a-9, I-a-10, I-a-18, I-a-19, I-a-22I-a-26-I-a-28, I-a-29, I-a-31, I-a-33, I-a-35, I-a-37, I-a-39, I-a-40,I-a-41, I-a-43, I-a-44, I-a-47, I-a-48, I-a-49, I-a-51, I-a-52, I-a-53,I-a-54, I-a-55, I-a-56, I-a-57, I-a-60, I-a-61, I-a-62, I-a-63, I-a-66,I-a-67, I-a-70, I-b-2, I-b-3, I-b-6, I-b-7, I-b-8, I-b-12, I-b-13,I-b-17, I-b-20, I-b-21, I-b-23, I-b-24, I-b-25, I-b-26, I-b-10, I-c-11,I-c-12, I-c-13, I-c-14, I-c-15, I-c-16, I-c-17, I-c-20, I-c-24, I-c-27,I-c-31, I-c-36

Example No. 3 Phaedon Test PHAECO Spray Treatment

Solvents:

-   -   78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide        Emulsifier:    -   0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of Chinese cabbage (Brassica pekinensis) are sprayed with anactive compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After the desired period of time, the effect in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an efficacy of ≧80%:

Ex. No. I-a-4, I-a-6, I-a-11, I-a-14, I-a-29, I-a-30, I-a-34, I-a-35,I-c-4, I-b-2, I-b-3, I-b-21, I-b-23, I-b-25, I-a-27, I-a-41, I-a-44,I-a-49, I-a-50, I-c-2, I-c-13, I-c-25, I-c-27, I-c-29, I-c-33

Example No. 4 Nilaparvata lugens Test NILALU Hydroponic Treatment

Solvents:

-   -   78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide        Emulsifier:    -   0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

The active compound preparation is pipetted into water. The statedconcentration refers to the amount of active compound per volume unit ofwater (mg/l=ppm); the infection with the rice brown planthopper(Nilaparvata lugens) is then carried out.

After the desired period of time, the effect in % is determined. 100%means that all rice planthoppers have been killed; 0% means that none ofthe rice planthoppers have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at a concentration of 500 ppm after 7 d, an efficacy of≧80%: I-a-4.

Example No. 5 Spodoptera frugiperda Test SPODFR Spray Treatment

Solvents:

-   -   78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide        Emulsifier:    -   0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of maize leaves (Zea mays) are sprayed with an active compoundpreparation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After the desired period of time, the effect in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha of a.i. after 7 d, anefficacy of ≧80%: I-a-6, I-a-34, I-b-2, I-b-3, I-c-2, I-c-4.

Example No. 6 Meloidogyne Test MELGIN Spray Treatment

Solvent:

-   -   80 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent, and theconcentrate is diluted with water to the desired concentration.

Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

After the desired period of time, the nematicidal activity is determinedin % by the formation of galls. 100% means that no galls were found; 0%means that the number of galls on the treated plants corresponds to thatof the untreated control.

In this test, for example, the following compounds of the PreparationExamples show an activity of ≧80% at an application rate of 20 ppm:

Ex. No. I-a-49, I-a-50, I-b-25, I-c-22

Example No. 7 Nephotettix Test NEPHCI

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into theactive compound preparation of the desired concentration and populatedwith the green rice leafhopper (Nephotettix cincticeps) while the leavesare still moist.

After the desired period of time, the kill in % is determined. 100%means that all leafhoppers have been killed; 0% means that none of theleafhoppers have been killed.

In this test, for example, the following compounds of the PreparationExamples show an activity of ≧80% at an application rate of 100 ppm:

Ex. No. I-c-2

Example No. 8 Boophilus microplus Test BOOPMI Injection

Solvent: dimethyl sulphoxide

A suitable preparation of active compound is prepared by mixing 1 partby weight of active compound with the stated amount of solvent anddiluting the concentrate with solvent to the desired concentration.

The solution of active compound is injected into the abdomen (Boophilusmicroplus) and the animals are transferred into dishes and stored in aclimatized room.

After the desired period of time the effect in % is determined. In thiscase 100% means that none of the ticks has laid fertile eggs.

In this test, for example, the following compounds of the PreparationExamples show an activity of ≧80% when applied at a rate of 20μg/animal:

Ex. No. I-a-1, I-a-3, I-a-9, I-a-28, I-a-29, I-a-38, I-a-39, I-b-20,I-b-21, I-c-20

Example No. 9 Lucilia cuprina Test LUCICU

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of water and theconcentrate is diluted with water to the desired concentration.

Containers containing horsemeat treated with the active compoundpreparation of the desired concentration are populated with Luciliacuprina larvae.

After the desired period of time, the kill in % is determined. 100%means that all larvae have been killed; 0% means that none of the larvaehave been killed.

In this test, for example, the following compounds of the PreparationExamples show an activity of ≧80% at an application rate of 100 ppm:

Ex. No. I-a-29, I-a-38, I-b-21

Example 10 Herbicidal Pre-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy lawn in wood fibre pots and covered with soil. The testcompounds, formulated in the form of wettable powders (WP) or asemulsion concentrates (EC), are then, as an aqueous suspension with awater application rate of 800 l/ha (converted), with 0.2% of wettingagent added, applied to the surface of the covering soil.

After the treatment, the pots are placed in a greenhouse and kept undergood growth conditions for the test plants. The visual assessment of theemergence damage on the test plants is carried out after a trial periodof 3 weeks by comparison with the untreated controls (herbicidal effectin percent (%): 100% effect=the plants have died, 0% effect=like controlplants).

Herbicidal Post-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy lawn in wood fibre pots, covered with soil andcultivated in a greenhouse under good growth conditions. Two to threeweeks after sowing, the test plants are treated at the one-leaf stage.The test compounds, formulated as wettable powders (WP) or as emulsionconcentrates (EC), are then, as an aqueous suspension with a waterapplication rate of 800 l/ha (converted), with 0.2% of wetting agentadded, sprayed onto the green parts of the plants. After the test plantshave been kept in the greenhouse under optimum growth conditions forabout 3 weeks, the effect of the preparations is rated visually incomparison to untreated controls (herbicidal effect in percent (%): 100%effect=the plants have died, 0% effect=like control plants).

Applied by the pre-emergence method at 320 g/ha of a.i., the followingcompounds show an activity of ≧80% against Lolium multiflorum andSetaria viridis: I-a-2, I-a-22, I-a-25, I-a-26, I-a-27, I-a-29, I-a-38,I-a-39, I-a-46, I-a-49, I-a-50, I-a-51, I-a-52, I-a-54, I-a-57, I-a-59,I-a-60, I-a-61, I-a-62, I-a-63, I-a-64, I-a-65, I-a-66, I-a-67, I-a-68,I-a-70, I-b-13, I-b-15, I-b-17, I-b-21, I-b-22, I-b-24, I-b-25, I-b-26,I-c-16, I-c-18, I-c-22, I-c-26, I-c-29, I-c-30, I-c-31, I-c-32, I-c-33,I-c-34, I-c-35, I-c-36, I-c-37.

Applied by the post-emergence method at 80 g/ha of a.i., the followingcompounds show an activity of ≧70% against Echinochloa crus-galli,Lolium multiflorum and Setaria viridis and: I-a-24, I-a-26, I-a-37,I-a-46, I-a-49, I-a-50, I-a-51, I-a-54, I-a-58, I-a-59, I-a-60, I-a-61,I-a-63, I-a-64, I-a-65, I-a-66, I-a-67, I-a-68, I-b-25, I-c-32, I-c-37.

Post-Emergence Herbicidal Effect

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantsare placed in sandy loam soil in wood fibre pots or in plastic pots andare covered with earth and cultivated in a greenhouse and also, duringthe vegetation period, outdoors, outside of the greenhouse, under goodgrowth conditions. 2 to 3 weeks after sowing, the trial plants aretreated at the one- to three-leaf stage. The test compounds, formulatedas wettable powders (WP) or liquids (EC), are sprayed onto the plantsand the soil surface in various dosages, with a water application rateof 300 l/ha (converted) and with addition of wetting agent (0.2% to0.3%). 3 to 4 weeks after the trial plants have been treated, the effectof the products is rated visually in comparison to untreated controls(herbicidal effect in percent: 100% effect=plants have died, 0%effect=like control plants).

Use of Safeners

If the testing is also to look at whether safeners can improve thetolerance of the crop plants for test substances, the following optionsare used for the application of the safener:

-   -   seeds of the crop plants are dressed with the safener substance        prior to sowing (the amount of safener is stated as a        percentage, based on the seed weight)    -   crop plants are sprayed with the safener, with a defined        application rate per hectare, prior to application of the test        substances (typically 1 day before the test substances are        applied)    -   the safener is applied together with the test substance in the        form of a tank mix (the amount of safener is reported in g/ha or        as a proportion relative to the herbicide).

By comparing the effect of test substances on crop plants which havebeen treated with safener and without safener it is possible to assessthe effect of the safener substance.

Greenhouse Container Trials with Cereals Mefenpyr 1 Day Prior toHerbicide Application

10 days after application Application rate Summer wheat g of a.i./haobserved (%) (I-a-49) 100 40 50 20 25 10 (I-a-49) + 100 + 50  0 Mefenpyr50 + 50 0 25 + 50 0

28 days after application Application rate Summer barley Summer wheat gof a.i./ha observed (%) observed (%) (I-a-50) 100 60 70 50 50 60 25 3040 12.5 8 10 (I-a-50) + 100 + 50  30 20 Mefenpyr 50 + 50 10 5 25 + 50 50 12.5 + 50   0 0

10 days after application Application rate Summer barley Summer wheat gof a.i./ha observed (%) observed (%) (I-b-24) 100 30 40 50 30 40 25 2040 12.5 10 30 (I-b-24) + 100 + 50  10 20 Mefenpyr 50 + 50 8 10 25 + 50 55 12.5 + 50   5 0

28 days after application Application rate Summer wheat g of a.i./haobserved (%) (I-b-24) 100 20 50 20 (I-b-24) + 100 + 50 5 Mefenpyr  50 +50 5

10 days after application Application rate Summer wheat g of a.i./haobserved (%) (I-b-25) 100 20 (I-b-25) + 100 + 50 0 Mefenpyr

Example 12 Heliothis virescens Test Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soya bean shoots (Glycine max) of the cultivar Roundup Ready (trade markof Monsanto Comp. USA) are treated by being dipped into the preparationof active compound of the desired concentration and are populated withthe tobacco bud worm Heliothis virescens while the leaves are stillmoist.

After the desired period of time, the kill of the insects is determined.

Example 13 Critical Concentration Test/Soil Insects Treatment ofTransgenic Plants

Test insect: Diabrotica balteata—larvae in the soil

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is poured onto the soil. Here, theconcentration of the active compound in the preparation is virtuallyimmaterial; only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots, and these are allowed to stand at 20° C.

Immediately after the preparation, 5 pregerminated maize corns of thecultivar YIELD GUARD (trade mark of Monsanto Comp., USA) are placed intoeach pot. After 2 days, the appropriate test insects are placed into thetreated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% activity).

Example 14 Boosting of Penetration into the Plant by Ammonium Salts orPhosphonium Salts, and Synergistic Boosting of Penetration into thePlant by Ammonium/Phosphonium Salts in Combination with PenetrationPromoters

This test measured the penetration of active compounds throughenzymatically isolated cuticles of apple leaves.

The leaves used were cut in the fully developed state from apple treesof the Golden Delicious variety. The cuticles were isolated as follows:

-   -   first of all, leaf discs labelled on the underside with dye and        formed by punching were filled by means of vacuum infiltration        with a pectinase solution (0.2% to 2% strength) buffered to a pH        of between 3 and 4,    -   sodium azide was then added and    -   the leaf discs thus treated were left to stand until the        original leaf structure broke down and the non-cellular cuticle        underwent detachment.

After that, only those cuticles from the top leaf sides that were freefrom stomata and hairs were used. They were washed a number of times inalternation with water and with a buffer solution, pH 7. The cleancuticles obtained were, finally, applied to Teflon plaques, smoothedwith a gentle jet of air, and dried.

In the next step the cuticular membranes obtained in this way wereplaced in stainless steel diffusion cells (transport chambers) for thepurpose of membrane transport investigations. For these investigationsthe cuticles were placed centrally using tweezers on the edges of thediffusion cells, which were coated with silicone grease, and sealed witha ring, which was likewise greased. The arrangement had been chosen sothat the morphological outer side of the cuticles was directed outwards,in other words facing the air, while the original inner side was facingthe inside of the diffusion cell.

The diffusion cells were filled with a 30% strength ethyleneglycol/water solution. Penetration was determined by applying 10 μl ofthe spray liquor of the composition below to the outer side of each ofthe cuticles. The spray liquor is prepared using local mains water ofmedium hardness.

After the spray liquors had been applied, the water was evaporated andthen the chambers were inverted and placed in thermostated troughs, inwhich the temperature and humidity over the cuticles was adjustable bymeans of a gentle stream of air onto the cuticles, with the spraycoating (20° C., 60% rh). At regular intervals, samples were taken usingan autosampler, and the amount of active compound was determined usingHPLC.

The results of the experiment are apparent from the table below. Thenumbers stated represent average values from 5 to 6 measurements. It canclearly be seen that ammonium sulphate, even on its own, significantlyimproves the penetration, and that together with RME there is asuperadditive (synergistic) effect.

Penetration after 24 h/% Active EC + AS EC + RME EC + RME (1 g/l) +compound EC (1 g/l) (1 g/l) AS (1 g/l) Example I-a-73 0.9 2.8 2.9 34.60.2 g/l in water/acetone 6:4 Example I-a-49 0.24 0.6 1.4 26 0.2 g/l inwater/acetone 6:4 RME = Rapeseed oil methyl ester (formulated for use as500 EW, concentration figure in g of active compound/l) AS = ammoniumsulphate EC = emulsifiable concentrate

Example 15 Activity Boost Through Ammonium/Phosphonium Salts Myzuspersicae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. For application with ammonium salts or phosphonium saltsthese are added in a concentration of 1000 ppm a.i. to the spray liquor.

Bell pepper plants (Capsicum annuum) which are heavily infested by theGreen peach aphid (Myzus persicae) are treated with the active compoundpreparation of the desired concentration by spraying to runoff point.After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

TABLE Active Active compound Kill rate/% after 6 days compound ppm +AS(1000 ppm) I-a-32 20 0 85 I-a-39 20 10 40 AS = ammonium sulphate

Example 16 Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration. For application with ammonium saltsor phosphonium salts these are added in a concentration of 1000 ppm a.i.to the spray liquor.

Cotton plants (Gossypium hirsutum) heavily infested by the cotton aphid(Aphis gossypii) are sprayed to runoff with the preparation of activecompound at the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

TABLE Active Active compound Kill rate/% after 6 days compound ppm +AS(1000 ppm) I-a-9 20 65 85 I-a-29 20 70 85 I-a-29 4 5 70

Example 17 Activity Boost Through Ammonium/Phosphonium Salts inCombination with Penetration Promoters Myzus persicae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. For application with ammonium salts or phosphonium saltsand penetration promoters (rapeseed oil methyl ester 500 EW) these arein each case added in a concentration of 1000 ppm to the spray liquor.

Bell pepper plants (Capsicum annuum) heavily infested by the green peachaphid (Myzus persicae) are sprayed to runoff with the preparation ofactive compound at the desired concentration. After the desired time,the kill in % is determined. 100% means that all of the animals havebeen killed; 0% means that no animals have been killed.

TABLE Kill rate/% after 6 days Active +AS +RME +RME + Active compound/(1000 (1000 AS (in each compound ppm ppm) ppm) case 1000 ppm) I-a-29 200 70 95 100

Example 18 Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration. For application with ammonium saltsor phosphonium salts and penetration promoters (rapeseed oil methylester 500 EW) these are in each case added in a concentration of 1000ppm a.i. to the spray liquor.

Cotton plants (Gossypium hirsutum) heavily infested by the cotton aphid(Aphis gossypii) are sprayed to runoff with the preparation of activecompound at the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

TABLE Kill rate/% after 6 days Active +AS +RME +RME + Active compound/(1000 (1000 AS (in each compound ppm ppm) ppm) case 1000 ppm) I-a-32 4 530 70 80

The invention claimed is:
 1. A compound of formula (I)

in which J represents trifluoromethoxy, X represents hydrogen, alkyl,halogen, haloalkyl, alkoxy or haloalkoxy, Y represents hydrogen, alkyl,alkoxy or halogen, with the proviso, that at least one of the radicalsJ, X and Y is located in the 2-position of the phenyl radical and is nothydrogen, A represents hydrogen, in each case optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl,saturated or unsaturated, optionally substituted cycloalkyl in whichoptionally at least one ring atom is replaced by a heteroatom, or ineach case optionally halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-,cyano- or nitro-substituted aryl, arylalkyl or hetaryl, B representshydrogen, alkyl or alkoxyalkyl, or A and B together with the carbon atomto which they are attached represent a saturated or unsaturated,unsubstituted or substituted cycle which optionally contains at leastone heteroatom, D represents hydrogen or an optionally substitutedradical from the group consisting of alkyl, alkenyl, alkynyl,alkoxyalkyl, saturated or unsaturated cycloalkyl in which optionally oneor more ring members are replaced by heteroatoms, arylalkyl, aryl,hetarylalkyl or hetaryl or A and D together with the atoms to which theyare attached represent a saturated or unsaturated cycle which optionallycontains at least one heteroatom and which is unsubstituted orsubstituted in the A, D moiety, G represents hydrogen (a) or representsone of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents in each case optionally halogen-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-,alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by atleast one heteroatom, in each case optionally substituted phenyl,phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents ineach case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,polyalkoxyalkyl or represents in each case optionally substitutedcycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵ independently of one anotherrepresent in each case optionally halogen-substituted alkyl, alkoxy,alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio orrepresent in each case optionally substituted phenyl, benzyl, phenoxy orphenylthio, R⁶ and R⁷ independently of one another represent hydrogen,in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,alkoxy, alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the nitrogen atom towhich they are attached represent a cycle which is optionallyinterrupted by oxygen or sulphur.
 2. A compound of the formula (I)according to claim 1 in which J represents trifluoromethoxy, Xrepresents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₆-alkoxyor C₁-C₄-haloalkoxy, Y represents hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy orhalogen, with the proviso, that at least one of the radicals J, X and Yis located in the 2-position of the phenyl radical and is not hydrogen,resulting in the phenyl substitution patterns below

where in the phenyl substitution patterns (C), (D), (E) and (K) X and Yare both not hydrogen simultaneously, A represents hydrogen or in eachcase optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, C₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionallyhalogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one or two not directly adjacent ring members arereplaced by oxygen and/or sulphur or represents in each case optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-,C₁-C₆-haloalkoxy-, cyano- or nitro-substituted phenyl, naphthyl, hetarylhaving 5 to 6 ring atoms, phenyl-C₁-C₆-alkyl or naphthyl-C₁-C₆-alkyl, Brepresents hydrogen, C₁-C₁₂-alkyl or C₁-C₈-alkoxy-C₁-C₆-alkyl or A, Band the carbon atom to which they are attached represent saturatedC₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkyl in which optionallyone ring member is replaced by oxygen or sulphur and which areoptionally mono- or disubstituted by C₁-C₈-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,C₃-C₆-cycloalkyl-C₁-C₂-alkoxy, C₃-C₁₀-cycloalkyl, C₁-C₈-haloalkyl,C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or phenyl or A, B and the carbonatom to which they are attached represent C₃-C₆-cycloalkyl which issubstituted by an alkylenediyl group which is optionally substituted byC₁-C₄-alkyl and optionally contains one or two not directly adjacentoxygen and/or sulphur atoms, or by an alkylenedioxyl or by analkylenedithioyl group which, together with the carbon atom to which itis attached, forms a further five- to eight-membered ring or A, B andthe carbon atom to which they are attached represent C₃-C₈-cyclo-alkylor C₅-C₈-cycloalkenyl in which two substituents together with the carbonatoms to which they are attached represent in each case optionallyC₁-C₆-alkyl-, C₁-C₆-alkoxy- or halogen-substituted C₂-C₆-alkanediyl,C₂-C₆-alkenediyl or C₄-C₆-alkanedienediyl in which optionally onemethylene group is replaced by oxygen or sulphur, D represents hydrogen,in each case optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkynyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl, optionally halogen-,C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C₄-haloalkyl-substitutedC₃-C₈-cycloalkyl in which optionally one ring member is replaced byoxygen or sulphur or in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-haloalkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, cyano- ornitro-substituted phenyl, hetaryl having 5 of 6 ring atoms,phenyl-C₁-C₆-alkyl or hetaryl-C₁-C₆-alkyl having 5 or 6 ring atoms or Aand D together represent in each case optionally substitutedC₃-C₆-alkanediyl or C₃-C₆-alkenediyl in which optionally one methylenegroup is replaced by a carbonyl group, oxygen or sulphur, possiblesubstituents being in each case: halogen, hydroxyl, mercapto or in eachcase optionally halogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₃-C₇-cycloalkyl, phenyl or benzyloxy, or a furtherC₃-C₆-alkanediyl grouping, C₃-C₆-alkenediyl grouping or a butadienylgrouping which is optionally substituted by C₁-C₆-alkyl or in whichoptionally two adjacent substituents together with the carbon atoms towhich they are attached form a further saturated or unsaturated cyclehaving 5 or 6 ring atoms which may contain oxygen or sulphur or whichoptionally contains one of the following groups

G represents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents in each case optionally halogen-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore not directly adjacent ring members are replaced by oxygen and/orsulphur, represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-haloalkyl-, C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio- orC₁-C₆-alkylsulphonyl-substituted phenyl, represents optionally halogen-,nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- orC₁-C₆-haloalkoxy-substituted phenyl-C₁-C₆-alkyl, represents optionallyhalogen- or C₁-C₆-alkyl-substituted 5- or 6-membered hetaryl, representsoptionally halogen- or C₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl orrepresents optionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryloxy-C₁-C₆-alkyl, R² represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, representsoptionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl or represents in each case optionally halogen-, cyano-,nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- orC₁-C₆-haloalkoxy-substituted phenyl or benzyl, R³ represents optionallyhalogen-substituted C₁-C₈-alkyl or represents in each case optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-,C₁-C₄-haloalkoxy-, cyano- or nitro-substituted phenyl or benzyl, R⁴ andR⁵ independently of one another represent in each case optionallyhalogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino,di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio, C₂-C₈-alkenylthio,C₃-C₇-cycloalkylthio or represent in each case optionally halogen-,nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-haloalkylthio-, C₁-C₄-alkyl- or C₁-C₄-haloalkyl-substitutedphenyl, phenoxy or phenyl-thio, R⁶ and R⁷ independently of one anotherrepresent hydrogen, represent in each case optionallyhalogen-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy,C₃-C₈-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-haloalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur, R¹³ represents hydrogen,represents in each case optionally halogen-substituted C₁-C₈-alkyl orC₁-C₈-alkoxy, represents optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur, or represents in eachcase optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-,C₁-C₄-haloalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy, R^(14a) represents hydrogenor C₁-C₈-alkyl or R¹³ and R^(14a) together represent C₄-C₆-alkanediyl,R^(15a) and R^(16a) are identical or different and represent C₁-C₆-alkylor R^(15a) and R^(16a) together represent a C₂-C₄-alkanediyl radicalwhich is optionally substituted by C₁-C₆-alkyl, C₁-C₆-haloalkyl or byoptionally halogen-, C₁-C₆-alkyl-, C₁-C₄-haloalkyl-, C₁-C₆-alkoxy-,C₁-C₄-haloalkoxy-, nitro- or cyano-substituted phenyl, R^(17a) andR^(18a) independently of one another preferably represent hydrogen,represent optionally halogen-substituted C₁-C₈-alkyl or representoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-,C₁-C₄-haloalkoxy-, nitro- or cyano-substituted phenyl or R^(17a) andR^(18a) together with the carbon atom to which they are attachedrepresent a carbonyl group or represent optionally halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₅-C₇-cycloalkyl in whichoptionally one methylene group is replaced by oxygen or sulphur, R^(19a)and R^(20a) independently of one another represent C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino,di-(C₁-C₁₀-alkyl)amino or di-(C₃-C₁₀-alkenyl)amino.
 3. A compound of theformula (I) according to claim 1 in which J represents trifluoromethoxy,X represents hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,trifluoromethyl or C₁-C₄-alkoxy, Y represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkoxy or C₁-C₄-alkyl, with the proviso, thatat least one of the radicals J, X and Y is located in the 2-position ofthe phenyl radical and is not hydrogen, resulting in the phenylsubstitution patterns below

where in the phenyl substitution patterns (C), (D), (E) and (K) X and Yare both not hydrogen simultaneously, A represents hydrogen, C₁-C₆-alkylor C₁-C₄-alkoxy-C₁-C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, represents C₃-C₆-cycloalkylwhich is optionally mono- or disubstituted by C₁-C₂-alkyl orC₁-C₂-alkoxy and which may optionally be interrupted by an oxygen atom,represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₂-haloalkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, cyano or nitro, Brepresents hydrogen, C₁-C₄-alkyl or C₁-C₂-alkoxyl-C₁-C₂-alkyl or A, Band the carbon atom to which they are attached represent saturated orunsaturated C₅-C₇-cycloalkyl in which optionally one ring member isreplaced by oxygen or sulphur and which is optionally mono- ordisubstituted by C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkoxy-C₁-C₂-alkoxy, C₃-C₆-cycloalkyl-methoxy, trifluoromethyl orC₁-C₆-alkoxy, or A, B and the carbon atom to which they are attachedC₅-C₆-cycloalkyl which is substituted by an alkylenediyl group which isoptionally substituted by methyl or ethyl and optionally contains one ortwo not directly adjacent oxygen and/or sulphur atoms, or by analkylenedioxyl or by an alkylenedithiol group which, together with thecarbon atom to which it is attached, forms a further five- toeight-membered ring, or A, B and the carbon atom to which they areattached represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twosubstituents together with the carbon atoms to which they are attachedrepresent in each case optionally C₁-C₂-alkyl- orC₁-C₂-alkoxy-substituted C₂-C₄-alkanediyl, C₂-C₄-alkenediyl orbutadiendiyl, D represents hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl orC₁-C₄-alkoxy-C₂-C₃-alkyl, each of which is optionally mono- totrisubstituted by fluorine, represents C₃-C₆-cycloalkyl which isoptionally mono- or disubstituted by C₁-C₄-alkyl, C₁-C₄-alkoxy orC₁-C₂-haloalkyl and in which optionally one methylene group is replacedby oxygen, or A and D together represent C₃-C₅-alkanediyl in which onemethylene group may be replaced by a carbonyl group, oxygen or sulphurand which may optionally be mono- or disubstituted, possiblesubstituents being C₁-C₂-alkyl or C₁-C₂-alkoxy or A and D together withthe atoms to which they are attached represent one of the groups AD-1 toAD-10:

G represents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents C₁-C₈-alkyl, C₂-C₁₈-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl orC₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, or C₃-C₆-cycloalkyl which isoptionally mono- or disubstituted by fluorine, chlorine, C₁-C₂-alkyl orC₁-C₂-alkoxy and in which optionally one or two not directly adjacentring members are replaced by oxygen, represents phenyl which isoptionally mono- or disubstituted by fluorine, chlorine, bromine, cyano,nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halo-alkyl or C₁-C₂-haloalkoxy,R² represents C₁-C₈-alkyl, C₂-C₈-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl,each of which is optionally mono- to trisubstituted by fluorine,represents C₃-C₆-cycloalkyl which is optionally monosubstituted byC₁-C₂-alkyl or C₁-C₂-alkoxy or represents phenyl or benzyl, each ofwhich is optionally mono- or disubstituted by fluorine, chlorine,bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₃-alkoxy, trifluoromethyl ortrifluoromethoxy, R³ represents C₁-C₆-alkyl which is optionally mono- totrisubstituted by fluorine or represents phenyl which is optionallymonosubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R⁴represents C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, C₃-C₄-alkenylthio,C₃-C₆-cycloalkylthio or represents phenyl, phenoxy or phenylthio, eachof which is optionally monosubstituted by fluorine, chlorine, bromine,nitro, cyano, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio,C₁-C₃-haloalkylthio, C₁-C₃-alkyl or trifluoromethyl, R⁵ representsC₁-C₆-alkoxy or C₁-C₆-alkylthio, R⁶ represents hydrogen, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,represents phenyl which is optionally monosubstituted by fluorine,chlorine, bromine, trifluoromethyl, C₁-C₄-alkyl or C₁-C₄-alkoxy,represents benzyl which is optionally monosubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, trifluoromethyl or C₁-C₄-alkoxy, R⁷represents C₁-C₆-alkyl, C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₁-C₄-alkyl, R⁶and R⁷ together represent an optionally methyl- or ethyl-substitutedC₄-C₅-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulphur.
 4. A compound of the formula (I)according to claim 1 in which J represents trifluoromethoxy, Xrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl,methoxy or ethoxy, Y represents hydrogen, chlorine, bromine, methyl,ethyl or methoxy, with the proviso, that at least one of the radicals J,X and Y is located in the 2-position of the phenyl radical and is nothydrogen, resulting in the phenyl substitution patterns below

where in the phenyl substitution patterns (G) and (H), X is nothydrogen, and in the phenyl substitution patterns (J), (K), (L), (M) and(N), X and Y are not hydrogen, A represents hydrogen, C₁-C₄-alkyl orC₁-C₂-alkoxy-C₁-C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine, represents cyclopropyl, cyclopentyl orcyclohexyl, represents in each case optionally fluorine-, chlorine-,bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenylor benzyl, B represents hydrogen, methyl or ethyl or A, B and the carbonatom to which they are attached represent saturated C₅-C₆-cycloalkyl inwhich optionally one ring member is replaced by oxygen or sulphur andwhich is optionally monosubstituted by methyl, ethyl, propyl, isopropyl,methoxymethyl, ethoxymethyl, propoxymethyl, trifluoromethyl, methoxy,ethoxy, propoxy, butoxy, methoxyethyl, ethoxyethyl, methoxyethoxy,ethoxyethoxy, cyclopropylmethoxy, cyclopentylmethoxy orcyclohexylmethoxy, or A, B and the carbon atom to which they areattached represent C₆-cycloalkyl which is optionally substituted by analkylenedioxyl group which contains two not directly adjacent oxygenatoms, or A, B and the carbon atom to which they are attached representC₅-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which two substituentstogether with the carbon atoms to which they are attached representC₂-C₄-alkanediyl or C₂-C₄-alkenediyl or butadienediyl, D representshydrogen, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₂-C₃-alkyl,represents cyclopropyl, cyclopentyl or cyclohexyl, each of which isoptionally mono- to trisubstituted by fluorine, or A and D together veryparticularly preferably represent C₃-C₅-alkanediyl which is optionallymonosubstituted by methyl or methoxy and in which optionally one carbonatom is replaced by oxygen or sulphur, or represent the group AD-1, Grepresents hydrogen (a) or represents one of the groups

in which L represents oxygen or sulphur, M represents oxygen or sulphurand E represents an ammonium ion, R¹ represents C₁-C₆-alkyl,C₂-C₁₇-alkenyl, C₁-C₂-alkoxy-C₁-alkyl, C₁-C₂-alkylthio-C₁-alkyl orrepresents cyclopropyl or cyclohexyl, each of which is optionallymonosubstituted by fluorine, chlorine, methyl or methoxy, representsphenyl which is optionally monosubstituted by fluorine, chlorine,bromine, cyano, nitro, methyl, methoxy, trifluoromethyl ortrifluoromethoxy, R² represents C₁-C₈-alkyl, C₂-C₆-alkenyl orC₁-C₄-alkoxy-C₂-C₃-alkyl, phenyl or benzyl, each of which is optionallymonosubstituted by fluorine, R³ represents C₁-C₈-alkyl.
 5. A compound ofthe formula (I) according to claim 1, in which J representstrifluoromethoxy, X represents hydrogen, chlorine, bromine, methyl,ethyl, or methoxy, Y represents hydrogen, chlorine, bromine, methyl ormethoxy, with the proviso, that at least one of the radicals J, X and Yis located in the 2-position of the phenyl radical and is not hydrogen,resulting in the phenyl substitution patterns below

where in the phenyl substitution patterns (G) and (H), X is nothydrogen, and in the phenyl substitution patterns (J) and (M), X and Yare not hydrogen, A represents C₁-C₄-alkyl or cyclopropyl, B representshydrogen or methyl, A, B and the carbon atom to which they are attachedrepresent saturated C₅-C₆-cycloalkyl in which optionally one ring memberis replaced by oxygen and which is optionally monosubstituted bymethoxymethyl, methoxy, ethoxy, propoxy or butoxy, or represent

D represents hydrogen or cyclopropyl, or A and D together representC₃-C₅-alkanediyl, G represents hydrogen (a) or one of the groups

R¹ represents C₁-C₆-alkyl, R² represents C₁-C₈-alkyl or benzyl.
 6. Aprocess for preparing a compound of the formula (I) according to claim1, characterized in that, (A) in order to obtain a compound of formula(I-a)

in which A, B, D, J, X and Y are as defined in claim 1, an N-acylaminoacid ester of formula (II)

in which A, B, D, J, X and Y are as defined in claim 1, and R⁸represents alkyl, is condensed intramolecularly in the presence of adiluent and in the presence of a base, (B) in order to obtain a compoundof formula (I-b)

in which A, B, D, J, R¹, X, and Y are as defined in claim 1, a compoundof the formula (I-a) in which A, B, D, J, X and Y are as defined inclaim 1 is in each case reacted (α) with an acid halide of formula (III)

in which R¹ is as defined in claim 1 and Hal represents halogen or (β)with a carboxylic anhydride of formula (IV)R¹—CO—O—CO—R¹  (IV) in which R¹ is as defined in claim 1, optionally inthe presence of a diluent and optionally in the presence of an acidbinder; (C) in order to obtain a compound of formula (I-c)

in which A, B, D, J, R², M, X and Y are as defined in claim 1 and Lrepresents oxygen, a compound of the formula (I-a) in which A, B, D, J,X and Y are as defined in claim 1 is in each case reacted with achloroformic ester or a chloroformic thioester of formula (V)R²-M-CO—Cl  (V) in which R² and M are as defined in claim 1, optionallyin the presence of a diluent and optionally in the presence of an acidbinder; (D) in order to obtain a compound of formula (I-c) in which A,B, D, J, R², M, X and Y are as defined in claim 1 and L representssulphur, a compound of the formula (I-a) in which A, B, D, J, X and Yare as defined in claim 1 is in each case reacted with achlormonothioformic ester or a chlordithioformic ester of formula (VI)

in which M and R² are as defined in claim 1, optionally in the presenceof a diluent and optionally in the presence of an acid binder and (E) inorder to obtain a compound of formula (I-d)

in which A, B, D, J, R³, X and Y are as defined in claim 1, a compoundof the formula (I-a) in which A, B, D, J, X and Y are as defined inclaim 1 is in each case reacted with a sulphonyl chloride of formula(VII)R³—SO₂—Cl  (VII) in which R³ is as defined in claim 1, optionally in thepresence of a diluent and optionally in the presence of an acid binder,(F) in order to obtain a compound of formula (I-e)

in which A, B, D, J, L, R⁴, R⁵, X and Y are as defined in claim 1, acompound of the formula (I-a) in which A, B, D, J, X and Y are asdefined in claim 1 is in each case reacted with a phosphorus compound offormula (VIII)

in which L, R⁴ and R⁵ are as defined in claim 1 and Hal representshalogen, optionally in the presence of a diluent and optionally in thepresence of an acid binder, (G) in order to obtain a compound of formula(I-f)

in which A, B, D, E, J, X and Y are as defined in claim 1, a compound ofthe formula (I-a) in which A, B, D, J, X and Y are as defined in claim 1is in each case reacted with a metal compound or an amine of formula(IX) and (X), respectively,

in which Me represents a mono- or divalent metal, or represents anammonium ion

t represents the number 1 or 2 and R¹⁰, R¹¹, R¹² independently of oneanother represent hydrogen or alkyl, optionally in the presence of adiluent, (H) in order to obtain a compound of formula (I-g)

in which A, B, D, J, L, R⁶, R⁷, X and Y are as defined in claim 1, acompound of the formula (I-a) in which A, B, D, J, X and Y are asdefined in claim 1 is in each case reacted (α) with an isocyanate or anisothiocyanate of formula (XI)R⁶—N═C=L  (XI) in which R⁶ and L are as defined in claim 1, optionallyin the presence of a diluent and optionally in the presence of acatalyst or (β) with a carbamoyl chloride or a thiocarbamoyl chloride offormula (XII)

in which L, R⁶ and R⁷ are as defined in claim 1, optionally in thepresence of a diluent and optionally in the presence of an acid binder.7. A composition for controlling pests, unwanted vegetation, orcombinations thereof, comprising at least one compound of the formula(I) according to claim
 1. 8. A method for controlling animal pests,unwanted vegetation, or combinations thereof, comprising allowing acompound of the formula (I) according to claim 1 to act on pests,unwanted vegetation, their habitat, or combinations thereof.
 9. Aprocess for preparing a composition for controlling pests, unwantedvegetation, or combinations thereof, comprising mixing a compound of theformula (I) according to claim 1 with an extender, a surfactant, or acombination thereof.
 10. A composition comprising an effective amount ofan active compound combination comprising, as components, (a′) at leastone trifluoromethoxyphenyl-substituted tetramic acid derivative of theformula (I) in which A, B, D, G, J, X and Y are as defined in claim 1and (b′) at least one crop plant compatibility-improving compoundselected from the group consisting of4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one(dicyclonon, BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl),3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),α-(cyanomethoximino)phenylacetonitrile (cyometrinil),2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyricacid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea(daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine(furilazole, MON-13900), ethyl4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),(4-chloro-o-tolyloxy)acetic acid (MCPA),2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),1,8-naphthalic anhydride,α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid,diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate,1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate,ethyl 5-chloroquinoline-8-oxyacetate, allyl5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate,diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid(AC-304415), 4-chlorophenoxyacetic acid,3,3′-dimethyl-4-methoxybenzophenone,1-bromo-4-chloromethylsulphonylbenzene,1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (also known asN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide),1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide,a compound of general formula (IIa),

a compound of general formula (IIb),

a compound of formula (IIc),

where m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of thedivalent heterocyclic groupings shown below

n represents a number 0, 1, 2, 3, 4 or 5, A² represents optionallyC₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl- and/orC₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbonatoms, R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy, C₁-C₆-alkenyloxy,C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino ordi(C₁-C₄-alkyl)-amino, R¹⁶ represents optionally fluorine-, chlorine-and/or bromine-substituted C₁-C₄-alkyl, R¹⁷ represents hydrogen, in eachcase optionally fluorine-, chlorine- and/or bromine-substitutedC₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl,piperidinyl, or optionally fluorine-, chlorine- and/or bromine- orC₁-C₄-alkyl-substituted phenyl, R¹⁸ represents hydrogen, in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl,piperidinyl, or optionally fluorine-, chlorine- and/or bromine- orC₁-C₄-alkyl-substituted phenyl, or R¹⁷ and R¹⁸ also together representC₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionallysubstituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring, or bytwo substituents which, together with the C atom to which they areattached, form a 5- or 6-membered carbocycle, R¹⁹ represents hydrogen,cyano, halogen, or represents in each case optionally fluorine-,chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, R²⁰ represents hydrogen, in each case optionally hydroxyl-,cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₃-C₆-cycloalkyl or tri-(C₁-C₄-alkyl)silyl, R²¹ represents hydrogen,cyano, halogen, or represents in each case optionally fluorine-,chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X² representshydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³ represents hydrogen, cyano, nitro,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,a compound of general formula (IId)

a compound of general formula (IIe)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0,1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl, R²³ representshydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,or in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio orC₃-C₆-cycloalkylamino, R²⁵ represents hydrogen, optionally cyano-,hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in eachcase optionally cyano- or halogen-substituted C₃-C₆-alkenyl orC₃-C₆-alkynyl, or optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, R²⁶ represents hydrogen, optionally cyano-, hydroxyl-,halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each caseoptionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl,optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,or optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together withR²⁵ represents in each case optionally C₁-C₄-alkyl-substitutedC₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, X⁴ represents nitro, cyano,carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and X⁵represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy.
 11. A composition according to claim 10 in which thecrop plant compatibility-improving compound is selected from the groupconsisting of cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron,


12. A composition according to claim 10, in which the crop plantcompatibility-improving compound is cloquintocet-mexyl.
 13. Acomposition according to claim 10, in which the crop plantcompatibility-improving compound is mefenpyr-diethyl.
 14. A method ofcontrolling unwanted vegetation, comprising allowing a compositionaccording to claim 10 to act on the plants, their surroundings, orcombinations thereof.
 15. A method of controlling unwanted vegetation,comprising allowing a compound of the formula (I) according to claim 1and the crop plant compatibility-improving compound selected from thegroup consisting of 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67,MON-4660),1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one(dicyclonon BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl),3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),α-(cyanomethoximino)phenylacetonitrile (cyometrinil),2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyricacid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea(daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine(furilazole, MON-13900), ethyl4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),(4-chloro-o-tolyloxy)acetic acid (MCPA),2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),1,8-naphthalic anhydride,α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid,diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate,ethyl 5-chloroquinoline-8-oxyacetate, allyl5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate,diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid(AC-304415), 4-chlorophenoxyacetic acid,3,3′-dimethyl-4-methoxybenzophenone,1-bromo-4-chloromethylsulphonylbenzene,1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (also known asN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide),1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide,a compound of general formula (IIa),

a compound of general formula (IIb),

a compound of formula (IIc),

where m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of thedivalent heterocyclic groupings shown below

n represents a number 0, 1, 2, 3, 4 or 5, A² represents optionallyC₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl- and/orC₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbonatoms, R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy, C₁-C₆-alkenyloxy,C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino ordi(C₁-C₄-alkyl)-amino, R¹⁶ represents optionally fluorine-, chlorine-and/or bromine-substituted R¹⁷ represents hydrogen, in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl,piperidinyl, or optionally fluorine-, chlorine- and/or bromine- orC₁-C₄-alkyl-substituted phenyl, R¹⁸ represents hydrogen, in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl,piperidinyl, or optionally fluorine-, chlorine- and/or bromine- orC₁-C₄-alkyl-substituted phenyl, or R¹⁷ and R¹⁸ also together representC₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionallysubstituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or bytwo substituents which, together with the C atom to which they areattached, form a 5- or 6-membered carbocycle, R¹⁹ represents hydrogen,cyano, halogen, or represents in each case optionally fluorine-,chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, R²⁰ represents hydrogen, in each case optionally hydroxyl-,cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₃-C₆-cycloalkyl or tri-(C₁-C₄-alkyl)silyl, R²¹ represents hydrogen,cyano, halogen, or represents in each case optionally fluorine-,chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X² representshydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³ represents hydrogen, cyano, nitro,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,a compound of general formula (IId)

a compound of general formula (IIe)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0,1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl, R²³ representshydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,or in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio orC₃-C₆-cycloalkylamino, R²⁵ represents hydrogen, optionally cyano-,hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in eachcase optionally cyano- or halogen-substituted C₃-C₆-alkenyl orC₃-C₆-alkynyl, or optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, R²⁶ represents hydrogen, optionally cyano-, hydroxyl-,halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each caseoptionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl,optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,or optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together withR²⁵ represents in each case optionally C₁-C₄-alkyl-substitutedC₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, X⁴ represents nitro, cyano,carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and X⁵represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy ofC₁-C₄-haloalkoxy to act, separately in close temporal succession, on theplants or their surroundings.
 16. A composition, comprising at least onecompound of the formula (I) according to claim 1 and at least one saltof the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, wherein the substituents areselected from the group consisting of halogen, nitro and cyano, nrepresents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.17. A composition according to claim 16, further comprising at least onepenetrant.
 18. A method of increasing the action of a pesticide, aherbicide, or a combination thereof, comprising preparing a ready-to-use(spray liquor) composition comprising an active compound of the formula(I) according to claim 1 and a salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, wherein the substituents areselected from the group consisting of halogen, nitro and cyano, nrepresents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.19. A method according to claim 18, wherein the spray liquor furthercomprises a penetrant.
 20. A composition, comprising a compositionaccording to claim 10 and at least one salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, wherein the substituents areselected from the group consisting of halogen, nitro and cyano, nrepresents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.21. A method of increasing the action of a pesticide, a herbicide, or acombination thereof, comprising preparing a ready-to-use (spray liquor)composition comprising a composition according to claim 10, and a saltof the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, wherein the substituents areselected from the group consisting of halogen, nitro and cyano, nrepresents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.